NO300325B1 - 1-substituerte 4-arylpiperidiner, mellomprodukter til fremstilling derav, farmasöytiske blandinger på basis derav, og anvendelse av dem - Google Patents
1-substituerte 4-arylpiperidiner, mellomprodukter til fremstilling derav, farmasöytiske blandinger på basis derav, og anvendelse av dem Download PDFInfo
- Publication number
- NO300325B1 NO300325B1 NO941906A NO941906A NO300325B1 NO 300325 B1 NO300325 B1 NO 300325B1 NO 941906 A NO941906 A NO 941906A NO 941906 A NO941906 A NO 941906A NO 300325 B1 NO300325 B1 NO 300325B1
- Authority
- NO
- Norway
- Prior art keywords
- piperidino
- piperidine
- compound
- formula
- hydroxy
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000000543 intermediate Substances 0.000 title abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 4
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 230000008485 antagonism Effects 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 166
- -1 methoxy , hydroxy, methylthio Chemical group 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 241000009298 Trigla lyra Species 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 92
- 230000008569 process Effects 0.000 abstract description 17
- 102100024304 Protachykinin-1 Human genes 0.000 abstract description 13
- 208000006673 asthma Diseases 0.000 abstract description 11
- 101000831616 Homo sapiens Protachykinin-1 Proteins 0.000 abstract description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 7
- 108060008037 tachykinin Proteins 0.000 abstract description 7
- 102000003141 Tachykinin Human genes 0.000 abstract description 6
- 230000009471 action Effects 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 210
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
- 238000005481 NMR spectroscopy Methods 0.000 description 128
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- 238000001819 mass spectrum Methods 0.000 description 117
- 239000000243 solution Substances 0.000 description 104
- 239000000463 material Substances 0.000 description 79
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 239000007787 solid Substances 0.000 description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 229910001868 water Inorganic materials 0.000 description 47
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 44
- 238000004587 chromatography analysis Methods 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 34
- 239000000047 product Substances 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 27
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 27
- 238000000746 purification Methods 0.000 description 26
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 25
- 239000012074 organic phase Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 22
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
- 102400000097 Neurokinin A Human genes 0.000 description 21
- 101800000399 Neurokinin A Proteins 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 238000010828 elution Methods 0.000 description 20
- 101000600912 Homo sapiens Substance-K receptor Proteins 0.000 description 19
- HEAUFJZALFKPBA-YRVBCFNBSA-N Neurokinin A Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-YRVBCFNBSA-N 0.000 description 19
- 239000012043 crude product Substances 0.000 description 18
- 239000003480 eluent Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000007792 addition Methods 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
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- 210000004027 cell Anatomy 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- LEEARGALTPRPLU-OAHLLOKOSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-oxobutyl]-n-methylbenzamide Chemical compound C1([C@H](CC=O)CN(C)C(=O)C=2C=CC=CC=2)=CC=C(Cl)C(Cl)=C1 LEEARGALTPRPLU-OAHLLOKOSA-N 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
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- 239000000443 aerosol Substances 0.000 description 12
- 239000000556 agonist Substances 0.000 description 12
- 230000027455 binding Effects 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000005909 Kieselgur Substances 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- FEKPQWCDELSHHJ-UHFFFAOYSA-N 2-piperidin-4-ylphenol Chemical compound OC1=CC=CC=C1C1CCNCC1 FEKPQWCDELSHHJ-UHFFFAOYSA-N 0.000 description 9
- ZDEWVCFSCQUKTE-UHFFFAOYSA-N 4-piperidin-4-ylphenol Chemical compound C1=CC(O)=CC=C1C1CCNCC1 ZDEWVCFSCQUKTE-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- VZOVOHRDLOYBJX-UHFFFAOYSA-N benzyl 4-oxopiperidine-1-carboxylate Chemical compound C1CC(=O)CCN1C(=O)OCC1=CC=CC=C1 VZOVOHRDLOYBJX-UHFFFAOYSA-N 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
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- 210000001519 tissue Anatomy 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
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- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 6
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- 230000004044 response Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- NONQCMNVMIGQEE-UHFFFAOYSA-N 4-(3-methoxyphenyl)piperidine Chemical compound COC1=CC=CC(C2CCNCC2)=C1 NONQCMNVMIGQEE-UHFFFAOYSA-N 0.000 description 5
- VCRQRAYQLAPLJH-UHFFFAOYSA-N 4-(4-methoxyphenyl)piperidine Chemical compound C1=CC(OC)=CC=C1C1CCNCC1 VCRQRAYQLAPLJH-UHFFFAOYSA-N 0.000 description 5
- SLYJXLIXZJYJBD-UHFFFAOYSA-N 4-(4-methylsulfanylphenyl)piperidine Chemical compound C1=CC(SC)=CC=C1C1CCNCC1 SLYJXLIXZJYJBD-UHFFFAOYSA-N 0.000 description 5
- 241000700198 Cavia Species 0.000 description 5
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
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- SRAVSVBVHDLLPO-UHFFFAOYSA-N 4-(2-methoxyphenyl)piperidine Chemical compound COC1=CC=CC=C1C1CCNCC1 SRAVSVBVHDLLPO-UHFFFAOYSA-N 0.000 description 4
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- GETHXZBPJVUSBH-UHFFFAOYSA-N 4-(2-methylsulfinylphenyl)piperidine Chemical compound CS(=O)C1=CC=CC=C1C1CCNCC1 GETHXZBPJVUSBH-UHFFFAOYSA-N 0.000 description 4
- WJGBOLJHUKMNLC-UHFFFAOYSA-N 4-(4-methylsulfinylphenyl)piperidine Chemical compound C1=CC(S(=O)C)=CC=C1C1CCNCC1 WJGBOLJHUKMNLC-UHFFFAOYSA-N 0.000 description 4
- UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 4
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- HLBCRWCVQFXQOE-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-4-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]butyl]-n-methylthiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)N(C)CC(C=1C=C(Cl)C(Cl)=CC=1)CCN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 HLBCRWCVQFXQOE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/24—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
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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)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939310713A GB9310713D0 (en) | 1993-05-24 | 1993-05-24 | Aryl substituted heterocycles |
Publications (3)
Publication Number | Publication Date |
---|---|
NO941906D0 NO941906D0 (no) | 1994-05-20 |
NO941906L NO941906L (no) | 1994-11-25 |
NO300325B1 true NO300325B1 (no) | 1997-05-12 |
Family
ID=10736057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO941906A NO300325B1 (no) | 1993-05-24 | 1994-05-20 | 1-substituerte 4-arylpiperidiner, mellomprodukter til fremstilling derav, farmasöytiske blandinger på basis derav, og anvendelse av dem |
Country Status (18)
Country | Link |
---|---|
US (1) | US5654299A (fr) |
EP (1) | EP0630887B1 (fr) |
JP (1) | JP3140294B2 (fr) |
CN (1) | CN1061977C (fr) |
AT (1) | ATE182583T1 (fr) |
AU (1) | AU673063B2 (fr) |
CA (1) | CA2124048A1 (fr) |
DE (1) | DE69419667T2 (fr) |
DK (1) | DK0630887T3 (fr) |
ES (1) | ES2135543T3 (fr) |
FI (1) | FI942381A (fr) |
GB (2) | GB9310713D0 (fr) |
GR (1) | GR3030875T3 (fr) |
HU (2) | HU216845B (fr) |
IL (3) | IL120895A (fr) |
NO (1) | NO300325B1 (fr) |
NZ (1) | NZ260566A (fr) |
RU (1) | RU2141947C1 (fr) |
Families Citing this family (59)
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US5583134A (en) * | 1992-09-30 | 1996-12-10 | Sanofi | 1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present |
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GB9325074D0 (en) * | 1993-12-07 | 1994-02-02 | Zeneca Ltd | Bicyclic heterocycles |
US5589489A (en) * | 1993-12-15 | 1996-12-31 | Zeneca Limited | Cyclic amide derivatives for treating asthma |
FR2719311B1 (fr) * | 1994-03-18 | 1998-06-26 | Sanofi Sa | Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic. |
FR2717802B1 (fr) * | 1994-03-25 | 1996-06-21 | Sanofi Sa | Nouveaux composés aromatiques, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
GB9408872D0 (en) * | 1994-05-03 | 1994-06-22 | Zeneca Ltd | Heterocyclic compounds |
TW432061B (en) * | 1994-08-09 | 2001-05-01 | Pfizer Res & Dev | Lactams |
EP0709375B1 (fr) * | 1994-10-25 | 2005-05-18 | AstraZeneca AB | Hétérocycles thérapeutiquement actifs |
US5998444A (en) * | 1995-10-24 | 1999-12-07 | Zeneca Ltd. | Piperidinyl compounds as NK1 or NK2 antagonists |
US6008223A (en) * | 1994-10-27 | 1999-12-28 | Zeneca Limited | Therapeutic compounds |
GB9421709D0 (en) * | 1994-10-27 | 1994-12-14 | Zeneca Ltd | Therapeutic compounds |
GB9502644D0 (en) * | 1995-02-10 | 1995-03-29 | Zeneca Ltd | Heterocyclic derivatives |
US5716970A (en) * | 1995-04-27 | 1998-02-10 | Pharmacia & Upjohn Company | Diuretic compound |
GB9508786D0 (en) | 1995-04-29 | 1995-06-21 | Zeneca Ltd | Substituted heterocycles |
US5688960A (en) * | 1995-05-02 | 1997-11-18 | Schering Corporation | Substituted oximes, hydrazones and olefins useful as neurokinin antagonists |
US5696267A (en) * | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
US5654316A (en) * | 1995-06-06 | 1997-08-05 | Schering Corporation | Piperidine derivatives as neurokinin antagonists |
FR2738245B1 (fr) * | 1995-08-28 | 1997-11-21 | Sanofi Sa | Nouveaux derives de piperidine, procede pour leur obtention et compositions pharmaceutiques les contenant |
GB9523526D0 (en) * | 1995-11-17 | 1996-01-17 | Zeneca Ltd | Therapeutic compounds |
HU224225B1 (hu) * | 1995-12-01 | 2005-06-28 | Sankyo Co. Ltd. | Tachikinin receptor antagonista hatású heterociklusos vegyületek, ezek előállítási eljárása és alkalmazásuk gyógyszerkészítmények előállítására |
IL125605A0 (en) * | 1996-02-21 | 1999-03-12 | Hoechst Marion Roussel Inc | Novel 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 |
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 |
ATE229952T1 (de) * | 1996-02-21 | 2003-01-15 | Aventis Pharma Inc | Substituierte n-methyl-n-(4-(piperidin-1-yl)-2- arylbutyl)-benzamide zur behandlung von allergischen erkrankungen |
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 |
CA2214288C (fr) * | 1996-09-18 | 2006-07-18 | Lonza Ag | Procede de preparation de 1-acyl-4-arylpiperidines |
US5789422A (en) * | 1996-10-28 | 1998-08-04 | Schering Corporation | Substituted arylalkylamines as neurokinin antagonists |
US5945428A (en) * | 1996-11-01 | 1999-08-31 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
CA2296314A1 (fr) * | 1997-07-25 | 1999-02-04 | Merck & Co., Inc. | Amines cycliques modulant l'activite des recepteurs de chimiokines |
TR200001437T2 (tr) * | 1997-11-21 | 2000-10-23 | Schering Corporation | Nörokinin muhasımlar olarak eşdeğer edilen oksimler. |
US6316445B1 (en) | 1998-05-15 | 2001-11-13 | Aventis Pharmaceuticals Inc. | Carboxy substituted acylic carboxamide derivatives |
EP1087963B1 (fr) | 1998-06-19 | 2004-08-25 | Chiron Corporation | Inhibiteurs de glycogene synthase kinase 3 |
US7045519B2 (en) | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
JP2002520316A (ja) | 1998-07-10 | 2002-07-09 | アストラゼネカ・アクチエボラーグ | ニューロキニン受容体アンタゴニストとしてのn−置換ナフタレンカルボキサミド |
GB9922521D0 (en) * | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
GB9922519D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
GB9924141D0 (en) * | 1998-10-30 | 1999-12-15 | Zeneca Ltd | Treatment of gastric asthma |
US6063926A (en) * | 1998-11-18 | 2000-05-16 | Schering Corporation | Substituted oximes as neurokinin antagonists |
GB9826941D0 (en) | 1998-12-09 | 1999-02-03 | Zeneca Pharmaceuticals | Compounds |
PE20001420A1 (es) * | 1998-12-23 | 2000-12-18 | Pfizer | Moduladores de ccr5 |
US7217714B1 (en) * | 1998-12-23 | 2007-05-15 | Agouron Pharmaceuticals, Inc. | CCR5 modulators |
EP1013276A1 (fr) | 1998-12-23 | 2000-06-28 | Pfizer Inc. | Aminoazacycloalcanes comme modulateurs de CCR5 |
US6667314B2 (en) | 2000-05-26 | 2003-12-23 | Pfizer, Inc. | Tropane derivatives useful in therapy |
ME00555B (me) * | 2000-05-26 | 2011-12-20 | Pfizer | Derivati tropana i njihova primj ena |
SE0103795D0 (sv) * | 2001-11-02 | 2001-11-02 | Astrazeneca Ab | Compounds and method for the treatment of överactive bladder |
SE0103668D0 (sv) * | 2001-11-02 | 2001-11-02 | Astrazeneca Ab | Method for the treatment of overactive blader |
EP1558250A4 (fr) * | 2002-10-30 | 2006-11-02 | Merck & Co Inc | Modulateurs gamma-aminoamides de l'activite de recepteur de chimiokine |
TW200508221A (en) | 2003-06-13 | 2005-03-01 | Astrazeneca Ab | New azetidine compounds |
US20040265238A1 (en) | 2003-06-27 | 2004-12-30 | Imtiaz Chaudry | Inhalable formulations for treating pulmonary hypertension and methods of using same |
AR057828A1 (es) | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
AR056087A1 (es) * | 2005-09-29 | 2007-09-19 | Astrazeneca Ab | Derivados de azetidina como antagonistas de receptores de neuroquina nk |
US8106208B2 (en) | 2006-05-18 | 2012-01-31 | Albireo Ab | Benzamide compounds that act as NK receptor antagonists |
US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
KR20100033419A (ko) | 2007-07-19 | 2010-03-29 | 메타볼렉스, 인코포레이티드 | 당뇨병 및 대사 장애의 치료를 위한 rup3 또는 gpr119 수용체의 작용제로서 n-아자시클릭 치환된 피롤, 피라졸, 이미다졸, 트리아졸 및 테트라졸 유도체 |
AU2009271414A1 (en) * | 2008-06-20 | 2010-01-21 | Metabolex, Inc. | Aryl GPR119 agonists and uses thereof |
CA2775840C (fr) | 2009-10-01 | 2018-02-06 | Metabolex, Inc. | Sels de la tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine substituee |
CN103037843A (zh) | 2010-06-23 | 2013-04-10 | 麦它波莱克斯股份有限公司 | 5-乙基-2-{4-[4-(4-四唑-1-基-苯氧甲基)-噻唑-2-基]-哌啶-1-基}-嘧啶的组合物 |
WO2018026890A1 (fr) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Composés d'aryle d'oxyméthylène pour le traitement de maladies gastro-intestinales inflammatoires ou de troubles gastro-intestinaux |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891066A (en) * | 1957-08-14 | 1959-06-16 | Parke Davis & Co | 4,o-substituted phenyl 1 alkanol piperidines and esters thereof |
FI97540C (fi) * | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
IL99320A (en) * | 1990-09-05 | 1995-07-31 | Sanofi Sa | Arylalkylamines, their preparation and pharmaceutical preparations containing them |
FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
FR2676053B1 (fr) * | 1991-05-03 | 1993-08-27 | Sanofi Elf | Nouveaux composes dialkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
FR2676055B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
FR2688219B1 (fr) * | 1992-03-03 | 1994-07-08 | Sanofi Elf | Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant. |
GB9321557D0 (en) * | 1992-11-03 | 1993-12-08 | Zeneca Ltd | Carboxamide derivatives |
-
1993
- 1993-05-24 GB GB939310713A patent/GB9310713D0/en active Pending
-
1994
- 1994-04-18 US US08/228,822 patent/US5654299A/en not_active Expired - Fee Related
- 1994-05-09 GB GB9409138A patent/GB9409138D0/en active Pending
- 1994-05-20 DE DE69419667T patent/DE69419667T2/de not_active Expired - Fee Related
- 1994-05-20 AT AT94303607T patent/ATE182583T1/de not_active IP Right Cessation
- 1994-05-20 CA CA002124048A patent/CA2124048A1/fr not_active Abandoned
- 1994-05-20 NO NO941906A patent/NO300325B1/no not_active IP Right Cessation
- 1994-05-20 HU HU9401543A patent/HU216845B/hu not_active IP Right Cessation
- 1994-05-20 RU RU94024563A patent/RU2141947C1/ru active
- 1994-05-20 DK DK94303607T patent/DK0630887T3/da active
- 1994-05-20 ES ES94303607T patent/ES2135543T3/es not_active Expired - Lifetime
- 1994-05-20 EP EP94303607A patent/EP0630887B1/fr not_active Expired - Lifetime
- 1994-05-20 HU HU9802402A patent/HU221295B1/hu not_active IP Right Cessation
- 1994-05-20 AU AU63203/94A patent/AU673063B2/en not_active Ceased
- 1994-05-20 NZ NZ260566A patent/NZ260566A/en unknown
- 1994-05-23 FI FI942381A patent/FI942381A/fi not_active Application Discontinuation
- 1994-05-23 IL IL12089594A patent/IL120895A/en not_active IP Right Cessation
- 1994-05-23 IL IL10973494A patent/IL109734A/en not_active IP Right Cessation
- 1994-05-24 JP JP06110008A patent/JP3140294B2/ja not_active Expired - Fee Related
- 1994-05-24 CN CN94106194A patent/CN1061977C/zh not_active Expired - Fee Related
-
1997
- 1997-05-22 IL IL12089597A patent/IL120895A0/xx unknown
-
1999
- 1999-07-29 GR GR990401829T patent/GR3030875T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
NO941906L (no) | 1994-11-25 |
JPH06340625A (ja) | 1994-12-13 |
GR3030875T3 (en) | 1999-11-30 |
AU6320394A (en) | 1994-12-15 |
ES2135543T3 (es) | 1999-11-01 |
EP0630887A1 (fr) | 1994-12-28 |
HU9401543D0 (en) | 1994-08-29 |
AU673063B2 (en) | 1996-10-24 |
NO941906D0 (no) | 1994-05-20 |
IL120895A (en) | 1998-09-24 |
DE69419667T2 (de) | 2000-04-06 |
CN1098094A (zh) | 1995-02-01 |
ATE182583T1 (de) | 1999-08-15 |
CN1061977C (zh) | 2001-02-14 |
JP3140294B2 (ja) | 2001-03-05 |
RU2141947C1 (ru) | 1999-11-27 |
GB9310713D0 (en) | 1993-07-07 |
DK0630887T3 (da) | 2000-03-06 |
FI942381A (fi) | 1994-11-25 |
HU216845B (hu) | 1999-09-28 |
NZ260566A (en) | 1996-07-26 |
IL109734A (en) | 1998-09-24 |
CA2124048A1 (fr) | 1994-11-25 |
IL120895A0 (en) | 1997-09-30 |
HUT70445A (en) | 1995-10-30 |
EP0630887B1 (fr) | 1999-07-28 |
HU221295B1 (en) | 2002-09-28 |
DE69419667D1 (de) | 1999-09-02 |
GB9409138D0 (en) | 1994-06-29 |
FI942381A0 (fi) | 1994-05-23 |
US5654299A (en) | 1997-08-05 |
IL109734A0 (en) | 1994-08-26 |
HU9802402D0 (en) | 1998-12-28 |
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Legal Events
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MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN NOVEMBER 2003 |