ZA200501164B - Novel amide compounds with MCH antagonistic effect and medicaments comprising said compounds - Google Patents
Novel amide compounds with MCH antagonistic effect and medicaments comprising said compounds Download PDFInfo
- Publication number
- ZA200501164B ZA200501164B ZA200501164A ZA200501164A ZA200501164B ZA 200501164 B ZA200501164 B ZA 200501164B ZA 200501164 A ZA200501164 A ZA 200501164A ZA 200501164 A ZA200501164 A ZA 200501164A ZA 200501164 B ZA200501164 B ZA 200501164B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- chloro
- group
- amino
- Prior art date
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- -1 amide compounds Chemical class 0.000 title claims description 174
- 150000001875 compounds Chemical class 0.000 title claims description 76
- 239000003814 drug Substances 0.000 title description 4
- 230000003042 antagnostic effect Effects 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 63
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 57
- 239000013543 active substance Substances 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 41
- 208000008589 Obesity Diseases 0.000 claims description 38
- 235000020824 obesity Nutrition 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000004122 cyclic group Chemical group 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 239000005557 antagonist Substances 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 230000037396 body weight Effects 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 230000002265 prevention Effects 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 206010003246 arthritis Diseases 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000020595 eating behavior Effects 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- 206010061428 decreased appetite Diseases 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000002249 Diabetes Complications Diseases 0.000 claims description 5
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 208000032841 Bulimia Diseases 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- 208000008967 Enuresis Diseases 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- FSIKNYBLCMZXIG-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-3-phenylpropanamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)CCC1=CC=CC=C1 FSIKNYBLCMZXIG-UHFFFAOYSA-N 0.000 claims description 4
- 206010029446 nocturia Diseases 0.000 claims description 4
- 208000020629 overactive bladder Diseases 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000002485 urinary effect Effects 0.000 claims description 4
- DTOABZXURMGIOT-NTEUORMPSA-N (e)-3-(4-chlorophenyl)-n-[2-[4-[2-(diethylamino)ethoxy]phenyl]ethyl]prop-2-enamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1CCNC(=O)\C=C\C1=CC=C(Cl)C=C1 DTOABZXURMGIOT-NTEUORMPSA-N 0.000 claims description 3
- BOBOYPLMAFCQBF-YRNVUSSQSA-N (e)-3-[2-chloro-4-(trifluoromethyl)phenyl]-n-[4-[2-(diethylamino)ethoxy]-3-methylphenyl]prop-2-enamide Chemical compound C1=C(C)C(OCCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl BOBOYPLMAFCQBF-YRNVUSSQSA-N 0.000 claims description 3
- LTBKLMGTYLNGEO-FRKPEAEDSA-N (e)-3-[4-(4-chlorophenyl)phenyl]-n-[4-[(dimethylamino)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)\C=C\C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 LTBKLMGTYLNGEO-FRKPEAEDSA-N 0.000 claims description 3
- VTAXNULCRKKEDX-CCEZHUSRSA-N (e)-3-[5-(4-chlorophenyl)pyridin-2-yl]-n-[4-(piperidin-1-ylmethyl)phenyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1C(C=N1)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1CN1CCCCC1 VTAXNULCRKKEDX-CCEZHUSRSA-N 0.000 claims description 3
- ACGPJODPKALIRX-QPJJXVBHSA-N (e)-n-[3-chloro-4-[(4-methylpiperidin-1-yl)methyl]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1CC(C)CCN1CC(C(=C1)Cl)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl ACGPJODPKALIRX-QPJJXVBHSA-N 0.000 claims description 3
- RLBWYNLTZOZBEZ-XVNBXDOJSA-N (e)-n-[3-chloro-4-[2-(4-methylpiperidin-1-yl)ethylamino]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1CC(C)CCN1CCNC(C(=C1)Cl)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl RLBWYNLTZOZBEZ-XVNBXDOJSA-N 0.000 claims description 3
- YSBBQHOKZFDFGX-JXMROGBWSA-N (e)-n-[3-chloro-4-[2-(diethylamino)ethyl]phenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C(Cl)C(CCN(CC)CC)=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1Cl YSBBQHOKZFDFGX-JXMROGBWSA-N 0.000 claims description 3
- QWYVXNDKCZOOIX-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[2-[4-[3-[ethyl-[(2-phenylacetyl)amino]amino]-2-hydroxypropoxy]phenyl]ethyl]acetamide Chemical compound C=1C=CC=CC=1CC(=O)NN(CC)CC(O)COC(C=C1)=CC=C1CCNC(=O)COC1=CC=C(Cl)C=C1 QWYVXNDKCZOOIX-UHFFFAOYSA-N 0.000 claims description 3
- VXQLYSVAPFBDDG-UHFFFAOYSA-N 2-[2-bromo-4-(trifluoromethyl)anilino]-n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1Br VXQLYSVAPFBDDG-UHFFFAOYSA-N 0.000 claims description 3
- YPXJIFIAUVZBOG-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[1-[2-(diethylamino)ethyl]indol-5-yl]acetamide Chemical compound C=1C=C2N(CCN(CC)CC)C=CC2=CC=1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl YPXJIFIAUVZBOG-UHFFFAOYSA-N 0.000 claims description 3
- HHBBGDQCDSTUKT-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]acetamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl HHBBGDQCDSTUKT-UHFFFAOYSA-N 0.000 claims description 3
- SCVALDNCXDIEKJ-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-nitrophenyl]acetamide Chemical compound C1=C([N+]([O-])=O)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl SCVALDNCXDIEKJ-UHFFFAOYSA-N 0.000 claims description 3
- 241001421185 Anomis Species 0.000 claims description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010007882 Cellulitis Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000027534 Emotional disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010020710 Hyperphagia Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 3
- 238000009825 accumulation Methods 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- BDEDBRLXJDUMGQ-UHFFFAOYSA-N ethyl 1-[2-[2-chloro-4-[[2-[2-chloro-4-(trifluoromethyl)phenoxy]acetyl]amino]phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl BDEDBRLXJDUMGQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000003054 hormonal effect Effects 0.000 claims description 3
- 230000003211 malignant effect Effects 0.000 claims description 3
- 208000008585 mastocytosis Diseases 0.000 claims description 3
- IOBQPWNCSJWLPO-UHFFFAOYSA-N methyl 2-[2-[2-chloro-4-[[2-(2,4-dichlorophenoxy)acetyl]amino]phenoxy]ethylamino]acetate Chemical compound C1=C(Cl)C(OCCNCC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1Cl IOBQPWNCSJWLPO-UHFFFAOYSA-N 0.000 claims description 3
- LFVWYJJSUKOMSH-UHFFFAOYSA-N n-[2-[[3-[4-[2-[[2-(4-chlorophenoxy)acetyl]amino]ethyl]phenoxy]-2-hydroxypropyl]amino]ethyl]-2-methylpropanamide Chemical compound C1=CC(OCC(O)CNCCNC(=O)C(C)C)=CC=C1CCNC(=O)COC1=CC=C(Cl)C=C1 LFVWYJJSUKOMSH-UHFFFAOYSA-N 0.000 claims description 3
- ZSPYBAOJTLYSGL-UHFFFAOYSA-N n-[3-chloro-4-(2-piperidin-1-ylethoxy)phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OCC(=O)NC(C=C1Cl)=CC=C1OCCN1CCCCC1 ZSPYBAOJTLYSGL-UHFFFAOYSA-N 0.000 claims description 3
- UBKSBCAKGNYPNZ-UHFFFAOYSA-N n-[3-chloro-4-[2-(2,5-dihydropyrrol-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OCC(=O)NC(C=C1Cl)=CC=C1OCCN1CC=CC1 UBKSBCAKGNYPNZ-UHFFFAOYSA-N 0.000 claims description 3
- HMXMRCCTPBHQMI-UHFFFAOYSA-N n-[3-chloro-4-[2-(4-hydroxypiperidin-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(O)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl HMXMRCCTPBHQMI-UHFFFAOYSA-N 0.000 claims description 3
- LAYSOXLTSYGETP-UHFFFAOYSA-N n-[3-chloro-4-[2-(4-methoxypiperidin-1-yl)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1CC(OC)CCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl LAYSOXLTSYGETP-UHFFFAOYSA-N 0.000 claims description 3
- KMWJKDHUGHCNHE-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-phenylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2C=CC=CC=2)C=C1Cl KMWJKDHUGHCNHE-UHFFFAOYSA-N 0.000 claims description 3
- RIIGCGDJQKRDTH-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-pyridin-3-ylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2C=NC=CC=2)C=C1Cl RIIGCGDJQKRDTH-UHFFFAOYSA-N 0.000 claims description 3
- PQFMDVQWZHNLML-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(2-chloro-4-thiophen-2-ylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C=2SC=CC=2)C=C1Cl PQFMDVQWZHNLML-UHFFFAOYSA-N 0.000 claims description 3
- RAFLGWWMXWKLFG-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-(4-iodo-2-methylphenoxy)acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(I)C=C1C RAFLGWWMXWKLFG-UHFFFAOYSA-N 0.000 claims description 3
- GEIZFQMGLCAAIY-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethoxy)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(OC(F)(F)F)C=C1Cl GEIZFQMGLCAAIY-UHFFFAOYSA-N 0.000 claims description 3
- RAANSKCNANFFCN-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1Cl RAANSKCNANFFCN-UHFFFAOYSA-N 0.000 claims description 3
- SLALFTXZLOYTLD-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethoxy]phenyl]-2-[2-fluoro-4-(trifluoromethyl)anilino]acetamide Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC=C1NC(=O)CNC1=CC=C(C(F)(F)F)C=C1F SLALFTXZLOYTLD-UHFFFAOYSA-N 0.000 claims description 3
- NLTXADYJUDHDAJ-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethyl]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(CCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl NLTXADYJUDHDAJ-UHFFFAOYSA-N 0.000 claims description 3
- CGDJONPRONXADL-UHFFFAOYSA-N n-[3-chloro-4-[2-(diethylamino)ethylamino]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(NCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl CGDJONPRONXADL-UHFFFAOYSA-N 0.000 claims description 3
- ATTBOTCOIGPWCI-UHFFFAOYSA-N n-[3-chloro-4-[3-(diethylamino)propoxy]phenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound C1=C(Cl)C(OCCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl ATTBOTCOIGPWCI-UHFFFAOYSA-N 0.000 claims description 3
- WROKVTPVZBKYHN-UHFFFAOYSA-N n-[4-(2-morpholin-4-ylethoxy)phenyl]-3-phenylpropanamide Chemical compound C=1C=C(OCCN2CCOCC2)C=CC=1NC(=O)CCC1=CC=CC=C1 WROKVTPVZBKYHN-UHFFFAOYSA-N 0.000 claims description 3
- RXFGWKWURLWMMY-UHFFFAOYSA-N n-[4-[2-[2-(aminomethyl)pyrrolidin-1-yl]ethoxy]-3-chlorophenyl]-2-[2-chloro-4-(trifluoromethyl)phenoxy]acetamide Chemical compound NCC1CCCN1CCOC(C(=C1)Cl)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl RXFGWKWURLWMMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 230000001850 reproductive effect Effects 0.000 claims description 3
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 3
- 208000015891 sexual disease Diseases 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 claims description 2
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 claims description 2
- ZTASNXVCHJIZNN-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)phenoxy]-n-[4-[2-(diethylamino)ethoxy]-3-methylphenyl]acetamide Chemical compound C1=C(C)C(OCCN(CC)CC)=CC=C1NC(=O)COC1=CC=C(C(F)(F)F)C=C1Cl ZTASNXVCHJIZNN-UHFFFAOYSA-N 0.000 claims description 2
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
- 150000002466 imines Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
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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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10250743A DE10250743A1 (de) | 2002-10-31 | 2002-10-31 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200501164B true ZA200501164B (en) | 2006-10-25 |
Family
ID=32115015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200501164A ZA200501164B (en) | 2002-10-31 | 2005-02-09 | Novel amide compounds with MCH antagonistic effect and medicaments comprising said compounds |
Country Status (24)
Country | Link |
---|---|
EP (1) | EP1558567B1 (fr) |
JP (1) | JP2006504761A (fr) |
KR (1) | KR20050065654A (fr) |
CN (1) | CN1708476A (fr) |
AR (1) | AR041735A1 (fr) |
AT (1) | ATE434601T1 (fr) |
AU (1) | AU2003285306A1 (fr) |
BR (1) | BR0315797A (fr) |
CA (1) | CA2504207C (fr) |
CO (1) | CO5570698A2 (fr) |
DE (2) | DE10250743A1 (fr) |
EA (1) | EA009040B1 (fr) |
EC (1) | ECSP055765A (fr) |
ES (1) | ES2327329T3 (fr) |
HR (1) | HRP20050383A2 (fr) |
MX (1) | MXPA05002865A (fr) |
NO (1) | NO20050745L (fr) |
PE (1) | PE20040785A1 (fr) |
PL (1) | PL376256A1 (fr) |
RS (1) | RS20050330A (fr) |
TW (1) | TW200412936A (fr) |
UY (1) | UY28051A1 (fr) |
WO (1) | WO2004039764A1 (fr) |
ZA (1) | ZA200501164B (fr) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
FR2866880A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Para-phenylenediamine secondaire n-alkylaminee ortho-et/ou meta-substituee, composition de teinture des fibres keratiniques contenant une telle para-phenylenediamine, procedes mettant en oeuvre cette composition et utilisations |
US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
JP2006076990A (ja) * | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
MX2009000334A (es) | 2006-08-25 | 2009-01-28 | Boehringer Ingelheim Int | Nuevos derivados de piridona con actividad antagonista de mch y medicamentos que comprenden estos compuestos. |
WO2008069611A1 (fr) * | 2006-12-08 | 2008-06-12 | Korea Research Institute Of Chemical Technology | Procédé de préparation de dérivées de n-phénylamide et composition prévenant ou traitant les troubles ischémiques les comprenant |
CL2007003580A1 (es) | 2006-12-11 | 2009-03-27 | Boehringer Ingelheim Int | Compuestos derivados de piridazina, antagonistas de mch; composicion farmaceutica que comprende a dicho compuesto; procedimiento de preparacion; y uso del compuesto en el tratamiento de trastornos metabolicos y/o trastornos alimentarios como obesidad, bulimia, anorexia, hiperfagia, diabetes. |
WO2010015680A1 (fr) * | 2008-08-07 | 2010-02-11 | Bayer Cropscience Sa | Dérivés fongicides de l'oxyalkylamide |
WO2010047982A1 (fr) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Nouveaux dérivés de benzimidazole cycliques utiles comme agents anti-diabétiques |
US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
CA2786314A1 (fr) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Nouveaux derives benzimidazole cycliques utiles comme agents antidiabetiques |
US9079880B2 (en) * | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
WO2012008549A1 (fr) | 2010-07-15 | 2012-01-19 | 武田薬品工業株式会社 | Composé hétérocyclique |
EP2677869B1 (fr) | 2011-02-25 | 2017-11-08 | Merck Sharp & Dohme Corp. | Nouveaux dérivés d'azabenzimidazole cyclique utiles en tant qu'agents antidiabétiques |
PE20141003A1 (es) * | 2011-07-29 | 2014-09-02 | Karyopharm Therapeutics Inc | Moduladores del transporte nuclear y usos de los mismos |
EA201490407A1 (ru) | 2011-07-29 | 2014-05-30 | Кариофарм Терапевтикс, Инк. | Содержащие гидразид модуляторы нуклеарного транспорта и их применения |
JP2015512913A (ja) | 2012-03-28 | 2015-04-30 | ザ ユナイテッド ステイツ オブ アメリカ, アズ リプレゼンテッド バイ ザ セクレタリー, デパートメント オブ ヘルス アンド ヒューマン サービシーズ | グルコセレブロシダーゼ活性剤として有用なサリチル酸誘導体 |
MX364992B (es) | 2012-05-09 | 2019-05-17 | Biogen Ma Inc | Moduladores del transporte nuclear y usos de los mismos. |
RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
CA2898482A1 (fr) | 2013-02-22 | 2014-08-28 | Linda L. Brockunier | Composes bicycliques antidiabetiques |
US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
WO2014144772A1 (fr) | 2013-03-15 | 2014-09-18 | Karyopharm Therapeutics Inc. | Procédés de promotion de la cicatrisation d'une plaie à l'aide d'inhibiteurs de crm1 |
PL3010892T3 (pl) | 2013-06-21 | 2019-07-31 | Karyopharm Therapeutics, Inc. | 1,2,4-triazole jako modulatory transportu jądrowego i ich zastosowania |
BR112015032370B1 (pt) * | 2013-06-27 | 2022-08-30 | Lg Chem, Ltd | Derivado de biarila, composição, e, método para preparar uma composição |
WO2015051496A1 (fr) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Composés tricycliques antidiabétiques |
ES2926377T3 (es) | 2014-08-15 | 2022-10-25 | Karyopharm Therapeutics Inc | Polimorfos de selinexor |
CN105439914B (zh) * | 2014-09-17 | 2017-07-11 | 复旦大学 | 4‑氨酰基苯氧乙酰胺类化合物及其药物用途 |
CA2970011C (fr) | 2014-12-24 | 2021-08-03 | Lg Chem, Ltd. | Derive de biaryle utilisable en tant qu'agoniste du gpr120 |
JP6533997B2 (ja) * | 2014-12-26 | 2019-06-26 | 株式会社ヤクルト本社 | Znf143阻害活性を有する化合物およびその利用 |
EP3397634A1 (fr) | 2015-12-31 | 2018-11-07 | Karyopharm Therapeutics, Inc. | Modulateurs de transport nucléaire et leurs utilisations |
WO2017117529A1 (fr) | 2015-12-31 | 2017-07-06 | Karyopharm Therapeutics Inc. | Modulateurs de transport nucléaire et leurs utilisations |
SG11201807516UA (en) | 2016-03-17 | 2018-09-27 | Hoffmann La Roche | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
US11602530B2 (en) | 2016-11-28 | 2023-03-14 | Biogen Ma Inc. | CRM1 inhibitors for treating epilepsy |
US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
EP3558298A4 (fr) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | Composés de spirochromane antidiabétiques |
KR20220034818A (ko) | 2019-07-10 | 2022-03-18 | 바이엘 악티엔게젤샤프트 | 2-(페닐이미노)-1,3-티아졸리딘-4-온의 제조 방법 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1100495A4 (fr) * | 1998-07-28 | 2002-09-25 | Smithkline Beecham Corp | Propenamides tenant lieu de modulateurs de ccr5 |
AU7315700A (en) * | 1999-09-20 | 2001-04-24 | Takeda Chemical Industries Ltd. | Melanin concentrating hormone antagonist |
WO2002006245A1 (fr) * | 2000-07-05 | 2002-01-24 | Synaptic Pharmarceutical Corporation | Antagonistes selectifs des recepteurs (mch1) d'hormone-1 de concentration de la melanine et utilisation de ceux-ci |
US20030022891A1 (en) * | 2000-12-01 | 2003-01-30 | Anandan Palani | MCH antagonists and their use in the treatment of obesity |
CN100548291C (zh) * | 2001-10-25 | 2009-10-14 | 先灵公司 | 用于治疗肥胖的mch拮抗剂 |
-
2002
- 2002-10-31 DE DE10250743A patent/DE10250743A1/de not_active Withdrawn
-
2003
- 2003-10-28 CA CA2504207A patent/CA2504207C/fr not_active Expired - Lifetime
- 2003-10-28 KR KR1020057007663A patent/KR20050065654A/ko not_active Application Discontinuation
- 2003-10-28 AT AT03778292T patent/ATE434601T1/de active
- 2003-10-28 RS YUP-2005/0330A patent/RS20050330A/sr unknown
- 2003-10-28 MX MXPA05002865A patent/MXPA05002865A/es not_active Application Discontinuation
- 2003-10-28 EP EP03778292A patent/EP1558567B1/fr not_active Expired - Lifetime
- 2003-10-28 CN CNA2003801022366A patent/CN1708476A/zh active Pending
- 2003-10-28 PL PL03376256A patent/PL376256A1/xx not_active Application Discontinuation
- 2003-10-28 AU AU2003285306A patent/AU2003285306A1/en not_active Abandoned
- 2003-10-28 EA EA200500596A patent/EA009040B1/ru not_active IP Right Cessation
- 2003-10-28 DE DE50311640T patent/DE50311640D1/de not_active Expired - Lifetime
- 2003-10-28 ES ES03778292T patent/ES2327329T3/es not_active Expired - Lifetime
- 2003-10-28 WO PCT/EP2003/011933 patent/WO2004039764A1/fr active Application Filing
- 2003-10-28 BR BR0315797-0A patent/BR0315797A/pt not_active Expired - Fee Related
- 2003-10-28 JP JP2004547576A patent/JP2006504761A/ja active Pending
- 2003-10-29 PE PE2003001094A patent/PE20040785A1/es not_active Application Discontinuation
- 2003-10-29 UY UY28051A patent/UY28051A1/es not_active Application Discontinuation
- 2003-10-30 TW TW092130313A patent/TW200412936A/zh unknown
- 2003-10-31 AR ARP030103995A patent/AR041735A1/es not_active Suspension/Interruption
-
2005
- 2005-02-09 ZA ZA200501164A patent/ZA200501164B/en unknown
- 2005-02-11 NO NO20050745A patent/NO20050745L/no not_active Application Discontinuation
- 2005-04-27 EC EC2005005765A patent/ECSP055765A/es unknown
- 2005-04-29 HR HR20050383A patent/HRP20050383A2/xx not_active Application Discontinuation
- 2005-05-26 CO CO05051560A patent/CO5570698A2/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
TW200412936A (en) | 2004-08-01 |
WO2004039764A1 (fr) | 2004-05-13 |
JP2006504761A (ja) | 2006-02-09 |
EA009040B1 (ru) | 2007-10-26 |
EP1558567A1 (fr) | 2005-08-03 |
UY28051A1 (es) | 2004-05-31 |
RS20050330A (en) | 2007-12-31 |
MXPA05002865A (es) | 2005-05-27 |
AR041735A1 (es) | 2005-05-26 |
CA2504207C (fr) | 2012-10-02 |
DE10250743A1 (de) | 2004-05-19 |
EA200500596A1 (ru) | 2005-12-29 |
DE50311640D1 (de) | 2009-08-06 |
ECSP055765A (es) | 2005-07-06 |
PE20040785A1 (es) | 2004-12-23 |
BR0315797A (pt) | 2005-09-13 |
ATE434601T1 (de) | 2009-07-15 |
ES2327329T3 (es) | 2009-10-28 |
HRP20050383A2 (en) | 2006-08-31 |
NO20050745L (no) | 2005-05-23 |
EP1558567B1 (fr) | 2009-06-24 |
KR20050065654A (ko) | 2005-06-29 |
CO5570698A2 (es) | 2005-10-31 |
CA2504207A1 (fr) | 2004-05-13 |
CN1708476A (zh) | 2005-12-14 |
AU2003285306A1 (en) | 2004-05-25 |
PL376256A1 (en) | 2005-12-27 |
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