NO313550B1 - Pyrrolidinyl- og pyrrolinyl etylaminforbindelser som kappa- agonister og fremgangsmåte for fremstilling derav, samtfarmasöytisk preparat - Google Patents
Pyrrolidinyl- og pyrrolinyl etylaminforbindelser som kappa- agonister og fremgangsmåte for fremstilling derav, samtfarmasöytisk preparat Download PDFInfo
- Publication number
- NO313550B1 NO313550B1 NO19991294A NO991294A NO313550B1 NO 313550 B1 NO313550 B1 NO 313550B1 NO 19991294 A NO19991294 A NO 19991294A NO 991294 A NO991294 A NO 991294A NO 313550 B1 NO313550 B1 NO 313550B1
- Authority
- NO
- Norway
- Prior art keywords
- methylamino
- phenylethyl
- hydroxypyrrolidin
- propylbenzamide
- mhz
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 178
- 239000000556 agonist Substances 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 104
- 125000000719 pyrrolidinyl group Chemical group 0.000 title description 4
- KRRLFZPRZPZNPW-UHFFFAOYSA-N n-ethyl-2,3-dihydropyrrol-1-amine Chemical class CCNN1CCC=C1 KRRLFZPRZPZNPW-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 986
- 150000001875 compounds Chemical class 0.000 claims description 119
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 77
- 239000000460 chlorine Substances 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
- -1 hydroxy, methoxy Chemical group 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000012442 inert solvent Substances 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 102000048260 kappa Opioid Receptors Human genes 0.000 claims description 7
- 108020001588 κ-opioid receptors Proteins 0.000 claims description 7
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- TTZHTKJTUXXCEX-RYUDHWBXSA-N (2r)-2-[(3s)-3-fluoropyrrolidin-1-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC[C@H](F)C1 TTZHTKJTUXXCEX-RYUDHWBXSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- NWZKEQHPACLAPF-RYUDHWBXSA-N (2r)-2-[(3s)-3-chloropyrrolidin-1-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC[C@H](Cl)C1 NWZKEQHPACLAPF-RYUDHWBXSA-N 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000730 antalgic agent Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000005543 phthalimide group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- XXZDIDFBKZKGQB-VXGBXAGGSA-N (1s)-2-[(3r)-3-fluoropyrrolidin-1-yl]-1-phenylethanol Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1CC[C@@H](F)C1 XXZDIDFBKZKGQB-VXGBXAGGSA-N 0.000 claims description 3
- AOKXUMARJFHZNA-LBPRGKRZSA-N (2r)-2-(2,5-dihydropyrrol-1-yl)-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC=CC1 AOKXUMARJFHZNA-LBPRGKRZSA-N 0.000 claims description 3
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 230000003444 anaesthetic effect Effects 0.000 claims description 3
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- 206010003246 arthritis Diseases 0.000 claims description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- FVPPPNWXMSRIOO-AVVPKOCDSA-N 2-[3-[[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-methylamino]pyrrolidin-1-yl]benzamide Chemical compound C([C@@H](N(C)C1CN(CC1)C=1C(=CC=CC=1)C(N)=O)C=1C=CC=CC=1)N1CC[C@H](O)C1 FVPPPNWXMSRIOO-AVVPKOCDSA-N 0.000 claims description 2
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- 239000003193 general anesthetic agent Substances 0.000 claims description 2
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- 230000002265 prevention Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 185
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- 238000003756 stirring Methods 0.000 description 37
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
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- 150000005690 diesters Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005667 methoxymethylation reaction Methods 0.000 description 1
- SRTWVWWNAJKWMO-NFJZVGLOSA-N methyl 2-chloro-4-[methyl-[(1s)-2-[(3s)-3-(oxan-2-yloxy)pyrrolidin-1-yl]-1-phenylethyl]amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC=C1N(C)[C@@H](C=1C=CC=CC=1)CN1C[C@@H](OC2OCCCC2)CC1 SRTWVWWNAJKWMO-NFJZVGLOSA-N 0.000 description 1
- UFBBWBUASTWQMC-RBBKRZOGSA-N methyl 2-methoxy-4-[[(1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=CC=CC=1)N(C)C1=CC=C(C(=O)OC)C(OC)=C1 UFBBWBUASTWQMC-RBBKRZOGSA-N 0.000 description 1
- HQRLEOWXQZXRCR-FCHUYYIVSA-N methyl 3-[[(1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=CC=CC=1)N(C)C1=CC=CC(C(=O)OC)=C1 HQRLEOWXQZXRCR-FCHUYYIVSA-N 0.000 description 1
- DVAILAFZMUHEMP-UHFFFAOYSA-N methyl 3-fluoro-4-(methylamino)benzoate Chemical compound CNC1=CC=C(C(=O)OC)C=C1F DVAILAFZMUHEMP-UHFFFAOYSA-N 0.000 description 1
- LATRKEGGDFLKDP-SIKLNZKXSA-N methyl 3-fluoro-4-[[(1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=CC=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1F LATRKEGGDFLKDP-SIKLNZKXSA-N 0.000 description 1
- FKMZNQQOPCCUTD-UHFFFAOYSA-N methyl 3-fluoro-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C(F)=C1 FKMZNQQOPCCUTD-UHFFFAOYSA-N 0.000 description 1
- IAFKBTJFBOADGH-RBBKRZOGSA-N methyl 3-methoxy-4-[[(1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=CC=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1OC IAFKBTJFBOADGH-RBBKRZOGSA-N 0.000 description 1
- SXUWFAHIDCNUIG-UHFFFAOYSA-N methyl 4-(hydroxyamino)benzoate Chemical compound COC(=O)C1=CC=C(NO)C=C1 SXUWFAHIDCNUIG-UHFFFAOYSA-N 0.000 description 1
- DNJIUPCQPLUXDO-ZEQRLZLVSA-N methyl 4-[[(1r)-1-[3-(methoxymethoxy)phenyl]-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]ethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@@H](C=1C=C(OCOC)C=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1 DNJIUPCQPLUXDO-ZEQRLZLVSA-N 0.000 description 1
- KJHKUJYYQGDTDM-VXKWHMMOSA-N methyl 4-[[(1r)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@@H](C=1C=CC=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1 KJHKUJYYQGDTDM-VXKWHMMOSA-N 0.000 description 1
- XSZOPWSDBRDCKZ-FCHUYYIVSA-N methyl 4-[[(1s)-1-(3-chlorophenyl)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]ethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=C(Cl)C=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1 XSZOPWSDBRDCKZ-FCHUYYIVSA-N 0.000 description 1
- DNJIUPCQPLUXDO-BJKOFHAPSA-N methyl 4-[[(1s)-1-[3-(methoxymethoxy)phenyl]-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]ethyl]-methylamino]benzoate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=C(OCOC)C=CC=1)N(C)C1=CC=C(C(=O)OC)C=C1 DNJIUPCQPLUXDO-BJKOFHAPSA-N 0.000 description 1
- XYXRZUFYZQZEST-LOSJGSFVSA-N methyl 4-[[(1s)-2-[(3s)-3-[tert-butyl(dimethyl)silyl]oxypyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N(C)[C@@H](C=1C=CC=CC=1)CN1C[C@@H](O[Si](C)(C)C(C)(C)C)CC1 XYXRZUFYZQZEST-LOSJGSFVSA-N 0.000 description 1
- CEIVCXRHQZRKRY-AZUAARDMSA-N methyl 4-[[(1s)-2-[(3s)-3-fluoropyrrolidin-1-yl]-1-phenylethyl]-methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N(C)[C@@H](C=1C=CC=CC=1)CN1C[C@@H](F)CC1 CEIVCXRHQZRKRY-AZUAARDMSA-N 0.000 description 1
- DOMJYWCXCVFKCA-UHFFFAOYSA-N methyl 4-amino-3-fluorobenzoate Chemical compound COC(=O)C1=CC=C(N)C(F)=C1 DOMJYWCXCVFKCA-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- ZXMDPSJGMJCMNZ-VQTJNVASSA-N methyl 6-[[(1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-phenylethyl]-methylamino]pyridine-3-carboxylate Chemical compound C1[C@@H](OCOC)CCN1C[C@H](C=1C=CC=CC=1)N(C)C1=CC=C(C(=O)OC)C=N1 ZXMDPSJGMJCMNZ-VQTJNVASSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 230000001095 motoneuron effect Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 239000008183 oral pharmaceutical preparation Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010825 rotarod performance test Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IBPCT/IB96/00957 | 1996-09-18 | ||
PCT/IB1997/001021 WO1998012177A1 (en) | 1996-09-18 | 1997-08-21 | Pyrrolidinyl and pyrrolinyl ethylamine compounds as kappa agonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO991294D0 NO991294D0 (no) | 1999-03-17 |
NO991294L NO991294L (no) | 1999-03-17 |
NO313550B1 true NO313550B1 (no) | 2002-10-21 |
Family
ID=11004480
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19991294A NO313550B1 (no) | 1996-09-18 | 1999-03-17 | Pyrrolidinyl- og pyrrolinyl etylaminforbindelser som kappa- agonister og fremgangsmåte for fremstilling derav, samtfarmasöytisk preparat |
Country Status (38)
Country | Link |
---|---|
US (7) | US6201007B1 (hr) |
EP (1) | EP0934264B1 (hr) |
JP (2) | JP3195368B2 (hr) |
KR (1) | KR100339666B1 (hr) |
CN (1) | CN1237962A (hr) |
AP (1) | AP1016A (hr) |
AR (1) | AR008168A1 (hr) |
AT (1) | ATE249433T1 (hr) |
AU (1) | AU719895B2 (hr) |
BG (1) | BG64194B1 (hr) |
BR (1) | BR9711506A (hr) |
CA (1) | CA2266006C (hr) |
CO (1) | CO4920224A1 (hr) |
DE (1) | DE69724805T2 (hr) |
DK (1) | DK0934264T3 (hr) |
DZ (1) | DZ2309A1 (hr) |
EA (1) | EA001341B1 (hr) |
ES (1) | ES2205248T3 (hr) |
HR (1) | HRP970509A2 (hr) |
ID (1) | ID19611A (hr) |
IL (3) | IL147368A0 (hr) |
IS (1) | IS4992A (hr) |
MA (1) | MA26441A1 (hr) |
NO (1) | NO313550B1 (hr) |
NZ (1) | NZ334439A (hr) |
OA (1) | OA10996A (hr) |
PA (1) | PA8437201A1 (hr) |
PE (1) | PE109998A1 (hr) |
PL (1) | PL332546A1 (hr) |
PT (1) | PT934264E (hr) |
SK (1) | SK32799A3 (hr) |
TN (2) | TNSN97092A1 (hr) |
TR (1) | TR199900590T2 (hr) |
TW (1) | TW432047B (hr) |
UA (1) | UA60310C2 (hr) |
WO (1) | WO1998012177A1 (hr) |
YU (1) | YU13899A (hr) |
ZA (1) | ZA978358B (hr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999051587A1 (fr) | 1998-04-01 | 1999-10-14 | Ono Pharmaceutical Co., Ltd. | Derives de thiophene condenses et medicaments contenant ceux-ci comme principe actif |
EP0982297A3 (en) * | 1998-08-24 | 2001-08-01 | Pfizer Products Inc. | Process for the preparation of hydroxy-pyrrolidinyl hydroxamic acid derivatives being opioid kappa receptor agonists |
AU2002247886A1 (en) * | 2001-04-30 | 2002-11-11 | Pfizer Products Inc. | Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists |
CA2477634A1 (en) * | 2002-02-28 | 2003-09-04 | Pfizer Products Inc. | Crystalline anhydrous and monohydrate benzoate salts of (2's,3s)-3-hydroxy-n-{2{n-methyl-n-4-(n-propylamino-carbonyl)phenyl]amino-2-phenyl}-ethylpyrrolidine |
AU2003269399A1 (en) * | 2002-11-01 | 2004-05-25 | Pfizer Products Inc. | Process for the preparation of pyrrolidinyl ethylamine compounds via a copper-mediated aryl amination |
US7423147B2 (en) * | 2004-03-31 | 2008-09-09 | Janssen Pharmaceutical, N.V. | Pyridine compounds as histamine H3 modulators |
US7746514B2 (en) * | 2004-04-14 | 2010-06-29 | Hung-Yi Hsu | Scanner and exposure control method thereof |
WO2007081978A2 (en) * | 2006-01-11 | 2007-07-19 | Angion Biomedica Corporation | Modulators of hepatocyte growth factor / c-met activity |
CA2653940C (en) | 2006-05-30 | 2015-07-14 | Janssen Pharmaceutica N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
AU2007265238A1 (en) * | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted benzamide modulators of the histamine H3 receptor |
CA2706328C (en) | 2007-11-20 | 2016-04-19 | Janssen Pharmaceutica N.V. | Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine h3 receptor |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8801304D0 (en) * | 1988-01-21 | 1988-02-17 | Ici Plc | Diamine compounds |
DE4034785A1 (de) * | 1990-11-02 | 1992-05-07 | Merck Patent Gmbh | 1-(2-arylethyl)-pyrrolidine |
US5232978A (en) * | 1988-12-23 | 1993-08-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 1-(2-arylethyl)-pyrrolidines |
DE3935371A1 (de) | 1988-12-23 | 1990-07-05 | Merck Patent Gmbh | Stickstoffhaltige ringverbindungen |
WO1994018165A1 (en) | 1993-02-12 | 1994-08-18 | Pfizer Inc. | Sulfonamide compounds as opioid k-receptor agonists |
IL117440A0 (en) | 1995-03-31 | 1996-07-23 | Pfizer | Pyrrolidinyl hydroxamic acid compounds and their production process |
-
1997
- 1997-05-27 TN TNTNSN97092A patent/TNSN97092A1/fr unknown
- 1997-08-20 TW TW086111948A patent/TW432047B/zh active
- 1997-08-21 EA EA199900209A patent/EA001341B1/ru not_active IP Right Cessation
- 1997-08-21 PT PT97934676T patent/PT934264E/pt unknown
- 1997-08-21 IL IL14736897A patent/IL147368A0/xx unknown
- 1997-08-21 US US09/254,805 patent/US6201007B1/en not_active Expired - Fee Related
- 1997-08-21 YU YU13899A patent/YU13899A/sh unknown
- 1997-08-21 CN CN97199817A patent/CN1237962A/zh active Pending
- 1997-08-21 PL PL97332546A patent/PL332546A1/xx unknown
- 1997-08-21 EP EP97934676A patent/EP0934264B1/en not_active Expired - Lifetime
- 1997-08-21 DE DE69724805T patent/DE69724805T2/de not_active Expired - Fee Related
- 1997-08-21 AU AU37812/97A patent/AU719895B2/en not_active Ceased
- 1997-08-21 NZ NZ334439A patent/NZ334439A/xx unknown
- 1997-08-21 TR TR1999/00590T patent/TR199900590T2/xx unknown
- 1997-08-21 IL IL12895997A patent/IL128959A0/xx unknown
- 1997-08-21 DK DK97934676T patent/DK0934264T3/da active
- 1997-08-21 IL IL14736797A patent/IL147367A0/xx unknown
- 1997-08-21 WO PCT/IB1997/001021 patent/WO1998012177A1/en not_active Application Discontinuation
- 1997-08-21 BR BR9711506A patent/BR9711506A/pt not_active Application Discontinuation
- 1997-08-21 SK SK327-99A patent/SK32799A3/sk unknown
- 1997-08-21 CA CA002266006A patent/CA2266006C/en not_active Expired - Fee Related
- 1997-08-21 ES ES97934676T patent/ES2205248T3/es not_active Expired - Lifetime
- 1997-08-21 UA UA99031459A patent/UA60310C2/uk unknown
- 1997-08-21 JP JP51443398A patent/JP3195368B2/ja not_active Expired - Fee Related
- 1997-08-21 AT AT97934676T patent/ATE249433T1/de not_active IP Right Cessation
- 1997-08-21 KR KR1019997002287A patent/KR100339666B1/ko not_active IP Right Cessation
- 1997-08-29 PA PA19978437201A patent/PA8437201A1/es unknown
- 1997-09-04 AR ARP970104054A patent/AR008168A1/es not_active Application Discontinuation
- 1997-09-11 AP APAP/P/1997/001082A patent/AP1016A/en active
- 1997-09-15 MA MA24796A patent/MA26441A1/fr unknown
- 1997-09-16 ID IDP973203A patent/ID19611A/id unknown
- 1997-09-16 TN TNTNSN97156A patent/TNSN97156A1/fr unknown
- 1997-09-17 CO CO97054286A patent/CO4920224A1/es unknown
- 1997-09-17 ZA ZA978358A patent/ZA978358B/xx unknown
- 1997-09-17 DZ DZ970159A patent/DZ2309A1/xx active
- 1997-09-18 PE PE1997000834A patent/PE109998A1/es not_active Application Discontinuation
- 1997-09-18 HR HRPCT/IB96/00957A patent/HRP970509A2/hr not_active Application Discontinuation
-
1999
- 1999-03-05 IS IS4992A patent/IS4992A/is unknown
- 1999-03-11 BG BG103239A patent/BG64194B1/bg unknown
- 1999-03-12 OA OA9900057A patent/OA10996A/en unknown
- 1999-03-17 NO NO19991294A patent/NO313550B1/no unknown
-
2001
- 2001-01-26 US US09/770,514 patent/US6294569B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,512 patent/US6303602B1/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,513 patent/US6313302B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/771,030 patent/US6294557B1/en not_active Expired - Fee Related
- 2001-01-26 US US09/771,029 patent/US6307061B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,515 patent/US6310061B2/en not_active Expired - Fee Related
- 2001-03-28 JP JP2001092342A patent/JP2001316344A/ja active Pending
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