NO330496B1 - Anvendelse av prolinderivater, farmasoytisk sammensetning samt prolinderivater - Google Patents

Info

Publication number

NO330496B1

NO330496B1 NO20051407A NO20051407A NO330496B1 NO 330496 B1 NO330496 B1 NO 330496B1 NO 20051407 A NO20051407 A NO 20051407A NO 20051407 A NO20051407 A NO 20051407A NO 330496 B1 NO330496 B1 NO 330496B1

Authority

NO

Norway

Prior art keywords

pyrrolidine

pain

formula

carboxylic acid

compounds

Prior art date

2002-10-31

Links

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• Global Dossier
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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
• 150000003147 proline derivatives Chemical class 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 208000002193 Pain Diseases 0.000 claims abstract description 51
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 230000036407 pain Effects 0.000 claims abstract description 46
• -1 cyano, nitro, amino, hydroxycarbonyl Chemical group 0.000 claims abstract description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
• 239000012453 solvate Substances 0.000 claims abstract description 16
• 208000035475 disorder Diseases 0.000 claims abstract description 15
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical class 0.000 claims abstract description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
• 208000009935 visceral pain Diseases 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• 206010015037 epilepsy Diseases 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
• 125000001424 substituent group Chemical group 0.000 claims abstract description 4
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 3
• 208000006083 Hypokinesia Diseases 0.000 claims abstract description 3
• 230000036506 anxiety Effects 0.000 claims abstract description 3
• 230000003483 hypokinetic effect Effects 0.000 claims abstract description 3
• 238000002360 preparation method Methods 0.000 claims description 61
• 239000003814 drug Substances 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 6
• 150000002431 hydrogen Chemical group 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
• 238000013160 medical therapy Methods 0.000 claims description 4
• LUANXJIOUGKVRZ-UWVGGRQHSA-N (2s,4s)-4-(3-chlorophenoxy)pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1OC1=CC=CC(Cl)=C1 LUANXJIOUGKVRZ-UWVGGRQHSA-N 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 208000005171 Dysmenorrhea Diseases 0.000 claims description 3
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 3
• 208000000450 Pelvic Pain Diseases 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 201000003146 cystitis Diseases 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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• 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• AKDCUWCBNFWCTN-QWRGUYRKSA-N (2s,4s)-4-(cyclohexylmethyl)pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1CC1CCCCC1 AKDCUWCBNFWCTN-QWRGUYRKSA-N 0.000 claims description 2
• CLZUEJYWLODNSW-CBAPKCEASA-N (2s,4s)-4-[(2,3-difluorophenoxy)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1COC1=CC=CC(F)=C1F CLZUEJYWLODNSW-CBAPKCEASA-N 0.000 claims description 2
• UPZSZIAAAGYKKQ-XVKPBYJWSA-N (2s,4s)-4-[(2,3-difluorophenyl)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1CC1=CC=CC(F)=C1F UPZSZIAAAGYKKQ-XVKPBYJWSA-N 0.000 claims description 2
• JYONFSGPGOMJGQ-XVKPBYJWSA-N (2s,4s)-4-[(2,5-difluorophenoxy)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1COC1=CC(F)=CC=C1F JYONFSGPGOMJGQ-XVKPBYJWSA-N 0.000 claims description 2
• RAQCCYPHNZQIOA-CPCISQLKSA-N (2s,4s)-4-[(2,5-difluorophenyl)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1CC1=CC(F)=CC=C1F RAQCCYPHNZQIOA-CPCISQLKSA-N 0.000 claims description 2
• YDCYESLFDOQQBS-KWQFWETISA-N (2s,4s)-4-[(3-fluorophenoxy)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1COC1=CC=CC(F)=C1 YDCYESLFDOQQBS-KWQFWETISA-N 0.000 claims description 2
• RGFRGRZSMVXTLF-ONGXEEELSA-N (2s,4s)-4-[(3-fluorophenyl)methyl]pyrrolidine-2-carboxylic acid Chemical compound C1N[C@H](C(=O)O)C[C@@H]1CC1=CC=CC(F)=C1 RGFRGRZSMVXTLF-ONGXEEELSA-N 0.000 claims description 2
• DRNMETWPIFAUPJ-CABZTGNLSA-N (2s,4s)-4-[(3-methoxyphenoxy)methyl]pyrrolidine-2-carboxylic acid Chemical compound COC1=CC=CC(OC[C@H]2C[C@H](NC2)C(O)=O)=C1 DRNMETWPIFAUPJ-CABZTGNLSA-N 0.000 claims description 2
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 230000002757 inflammatory effect Effects 0.000 claims description 2
• JYPQRTNZYVAOJR-KWQFWETISA-N methyl (2s,4s)-4-(3,4-dichlorophenoxy)pyrrolidine-2-carboxylate Chemical compound C1N[C@H](C(=O)OC)C[C@@H]1OC1=CC=C(Cl)C(Cl)=C1 JYPQRTNZYVAOJR-KWQFWETISA-N 0.000 claims description 2
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• 231100000889 vertigo Toxicity 0.000 claims description 2
• XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
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• 239000000651 prodrug Substances 0.000 abstract description 4
• 125000000217 alkyl group Chemical group 0.000 abstract description 3
• 125000003118 aryl group Chemical group 0.000 abstract description 3
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• 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
• 125000006823 (C1-C6) acyl group Chemical group 0.000 abstract 1
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 abstract 1
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 abstract 1
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 1
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• 239000000543 intermediate Substances 0.000 abstract 1
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
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