CN1037770C - 制备取代的噻唑基和取代的吡啶基衍生物的方法 - Google Patents
制备取代的噻唑基和取代的吡啶基衍生物的方法 Download PDFInfo
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- CN1037770C CN1037770C CN91104906A CN91104906A CN1037770C CN 1037770 C CN1037770 C CN 1037770C CN 91104906 A CN91104906 A CN 91104906A CN 91104906 A CN91104906 A CN 91104906A CN 1037770 C CN1037770 C CN 1037770C
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- 125000004076 pyridyl group Chemical group 0.000 title claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- -1 4-thiadiazolyl group Chemical group 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000003513 alkali Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000012442 inert solvent Substances 0.000 claims description 14
- 238000007126 N-alkylation reaction Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 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 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Chemical group 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical group 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 2
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- 125000003368 amide group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 4
- 208000026935 allergic disease Diseases 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 37
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000001035 drying Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
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- 238000006073 displacement reaction Methods 0.000 description 5
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 4
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- 239000003480 eluent Substances 0.000 description 4
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
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- 235000011056 potassium acetate Nutrition 0.000 description 1
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- 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
- C07D417/14—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 three or more hetero rings
-
- 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55432590A | 1990-07-19 | 1990-07-19 | |
| US554,325 | 1990-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1058216A CN1058216A (zh) | 1992-01-29 |
| CN1037770C true CN1037770C (zh) | 1998-03-18 |
Family
ID=24212925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91104906A Expired - Fee Related CN1037770C (zh) | 1990-07-19 | 1991-07-19 | 制备取代的噻唑基和取代的吡啶基衍生物的方法 |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0539420B1 (enExample) |
| JP (1) | JP3085707B2 (enExample) |
| KR (1) | KR100206723B1 (enExample) |
| CN (1) | CN1037770C (enExample) |
| AT (1) | ATE188477T1 (enExample) |
| AU (1) | AU646280B2 (enExample) |
| CA (1) | CA2086546A1 (enExample) |
| CZ (1) | CZ279903B6 (enExample) |
| DE (1) | DE69131895T2 (enExample) |
| DK (1) | DK0539420T3 (enExample) |
| ES (1) | ES2142802T3 (enExample) |
| FI (1) | FI102753B (enExample) |
| GR (1) | GR3032999T3 (enExample) |
| HU (1) | HU221298B1 (enExample) |
| IE (1) | IE912533A1 (enExample) |
| IL (1) | IL98865A (enExample) |
| MX (1) | MX9100307A (enExample) |
| NO (1) | NO304791B1 (enExample) |
| NZ (1) | NZ238863A (enExample) |
| PH (1) | PH31063A (enExample) |
| PL (1) | PL170580B1 (enExample) |
| PT (1) | PT98366B (enExample) |
| RU (1) | RU2067978C1 (enExample) |
| SK (1) | SK280690B6 (enExample) |
| TW (1) | TW209217B (enExample) |
| WO (1) | WO1992001697A1 (enExample) |
| ZA (1) | ZA915654B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2048109B1 (es) * | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
| US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| MXPA02000120A (es) | 1999-06-28 | 2002-07-02 | Janssen Pharmaceutica Nv | Inhibidores de la replicacion del virus sincitial respiratorio. |
| JP2003503403A (ja) | 1999-06-28 | 2003-01-28 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 呼吸合胞体ウイルス複製阻害剤 |
| EP1418175A1 (en) * | 1999-06-28 | 2004-05-12 | Janssen Pharmaceutica N.V. | Respiratory syncytial virus replication inhibitors |
| KR100756592B1 (ko) * | 1999-10-08 | 2007-09-10 | 그뤼넨탈 게엠베하 | 비사이클릭 이미다조-3-일-아민 유도체, 이의 제조방법 및 이를 포함하는 진통제 |
| RS20050532A (sr) | 2003-01-14 | 2007-12-31 | Arena Pharmaceuticals Inc., | Derivati 1,2,3-trisupstituisanog arila i heteroarila kao modulatori metabolizma za profilaksu i tretman poremećaja povezanih sa njim, kao što su dijebetes i hiperglikemija |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| RU2239637C1 (ru) * | 2003-07-17 | 2004-11-10 | Дж.Б.Кемикалс Энд Фармасьютикалс Лтд. | Улучшенный способ получения 5-[2-этокси-5-(4-метилпиперазин-1-илсульфонил)фенил]-1 метил-3-н-пропил-1,6-дигидро-7h-пиразол [4,3-d] пиримидин-7-она |
| RU2264814C2 (ru) * | 2003-12-29 | 2005-11-27 | Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") | Антигистаминная фармацевтическая композиция |
| AU2005245389A1 (en) * | 2004-05-12 | 2005-12-01 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| DE102004044884A1 (de) * | 2004-09-14 | 2006-05-24 | Grünenthal GmbH | Substituierte bizyklische Imidazo-3-yl-amin-Verbindungen |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| CN103221410B (zh) | 2010-09-22 | 2017-09-15 | 艾尼纳制药公司 | Gpr119受体调节剂和对与其相关的障碍的治疗 |
| EP3040334A1 (en) * | 2014-12-29 | 2016-07-06 | Faes Farma, S.A. | New benzimidazole derivatives as antihistamine agents |
| CA3002540C (en) | 2015-01-06 | 2023-11-07 | Arena Pharmaceuticals, Inc. | Use of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid for treating conditions related to the s1p1 receptor |
| JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１Ｐ１レセプター関連障害における使用のための（Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸（化合物１）の結晶性Ｌ−アルギニン塩 |
| JP7397011B2 (ja) | 2018-06-06 | 2023-12-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１ｐ１受容体に関連する状態を治療する方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206415A2 (en) * | 1985-06-24 | 1986-12-30 | Janssen Pharmaceutica N.V. | (4-Piperidinylmethyl and -hetero)purines |
| EP0297661A1 (en) * | 1987-07-01 | 1989-01-04 | Janssen Pharmaceutica N.V. | [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines |
| US4835161A (en) * | 1986-02-03 | 1989-05-30 | Janssen Pharmaceutica N.V. | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4556660A (en) * | 1982-07-12 | 1985-12-03 | Janssen Pharmaceutica N.V. | N-(Bicyclic heterocyclyl)-4-piperidinamines |
| US4634704A (en) * | 1983-10-06 | 1987-01-06 | Janssen Pharmaceutica, N.V. | Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines |
| US4695569A (en) * | 1983-11-30 | 1987-09-22 | Janssen Pharmaceutica N.V. | Bicyclic heterocyclyl containing N-(bicyclic heterocyclyl)-4-piperidinamines |
| US4695575A (en) | 1984-11-13 | 1987-09-22 | Janssen Pharmaceutica, N.V. | 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines |
| US4588722A (en) * | 1984-01-09 | 1986-05-13 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives |
| DE3701863A1 (de) * | 1987-01-23 | 1988-08-04 | Standard Elektrik Lorenz Ag | Sender zur kohaerent optischen nachrichtenuebertragung |
| US4897401A (en) * | 1987-06-19 | 1990-01-30 | Janssen Pharmaceutical N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases |
| GB8900380D0 (en) * | 1989-01-09 | 1989-03-08 | Janssen Pharmaceutica Nv | 2-aminopyrimidinone derivatives |
-
1991
- 1991-07-05 NZ NZ238863A patent/NZ238863A/xx unknown
- 1991-07-09 HU HU9300096A patent/HU221298B1/hu not_active IP Right Cessation
- 1991-07-09 DK DK91912667T patent/DK0539420T3/da active
- 1991-07-09 WO PCT/EP1991/001292 patent/WO1992001697A1/en not_active Ceased
- 1991-07-09 KR KR1019930700122A patent/KR100206723B1/ko not_active Expired - Fee Related
- 1991-07-09 RU RU9192016595A patent/RU2067978C1/ru not_active IP Right Cessation
- 1991-07-09 AT AT91912667T patent/ATE188477T1/de not_active IP Right Cessation
- 1991-07-09 EP EP91912667A patent/EP0539420B1/en not_active Expired - Lifetime
- 1991-07-09 PL PL91297612A patent/PL170580B1/pl not_active IP Right Cessation
- 1991-07-09 DE DE69131895T patent/DE69131895T2/de not_active Expired - Fee Related
- 1991-07-09 AU AU82093/91A patent/AU646280B2/en not_active Ceased
- 1991-07-09 ES ES91912667T patent/ES2142802T3/es not_active Expired - Lifetime
- 1991-07-09 CA CA002086546A patent/CA2086546A1/en not_active Abandoned
- 1991-07-09 JP JP03511645A patent/JP3085707B2/ja not_active Expired - Fee Related
- 1991-07-11 PH PH42771A patent/PH31063A/en unknown
- 1991-07-17 IL IL9886591A patent/IL98865A/en not_active IP Right Cessation
- 1991-07-18 SK SK2239-91A patent/SK280690B6/sk unknown
- 1991-07-18 ZA ZA915654A patent/ZA915654B/xx unknown
- 1991-07-18 PT PT98366A patent/PT98366B/pt not_active IP Right Cessation
- 1991-07-18 CZ CS912239A patent/CZ279903B6/cs not_active IP Right Cessation
- 1991-07-18 IE IE253391A patent/IE912533A1/en not_active Application Discontinuation
- 1991-07-19 CN CN91104906A patent/CN1037770C/zh not_active Expired - Fee Related
- 1991-07-19 MX MX9100307A patent/MX9100307A/es not_active IP Right Cessation
- 1991-08-03 TW TW080106084A patent/TW209217B/zh active
-
1993
- 1993-01-15 NO NO924313A patent/NO304791B1/no unknown
- 1993-01-18 FI FI930199A patent/FI102753B/fi active
-
2000
- 2000-03-21 GR GR20000400699T patent/GR3032999T3/el not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206415A2 (en) * | 1985-06-24 | 1986-12-30 | Janssen Pharmaceutica N.V. | (4-Piperidinylmethyl and -hetero)purines |
| US4835161A (en) * | 1986-02-03 | 1989-05-30 | Janssen Pharmaceutica N.V. | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines |
| EP0297661A1 (en) * | 1987-07-01 | 1989-01-04 | Janssen Pharmaceutica N.V. | [(Bicyclic heterocyclyl)methyl and -hetero] substituted hexahydro-1H-azepines and pyrrolidines |
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