CA2461144A1

CA2461144A1 - Preparation and use of pyrrole derivatives for treating obesity

Preparation and use of pyrrole derivatives for treating obesity Download PDF

Info

Publication number: CA2461144A1
Authority: CA; Canada
Prior art keywords: alkyl; hydroxy; alkoxy; compound; optionally substituted
Prior art date: 2001-09-24
Legal status : Abandoned

Application number

CA002461144A

Other languages

English (en)

French (fr)

Inventor

Roger A. Smith

Harold C. E. Kluender

Ning Su

Rico C. Lavoie

Jianmei Fan

Current Assignee

Bayer Pharmaceuticals Corp

Original Assignee

Individual

Priority date

2001-09-24

Filing date

2002-09-24

Publication date

2003-04-03

2002-09-24 Application filed by Individual filed Critical Individual

2003-04-03 Publication of CA2461144A1 publication Critical patent/CA2461144A1/en

Status Abandoned legal-status Critical Current

Links

208000008589 Obesity Diseases 0.000 title claims abstract description 40
235000020824 obesity Nutrition 0.000 title claims abstract description 39
150000003233 pyrroles Chemical class 0.000 title abstract description 6
238000002360 preparation method Methods 0.000 title description 18
150000001875 compounds Chemical class 0.000 claims abstract description 143
238000000034 method Methods 0.000 claims abstract description 75
239000000203 mixture Substances 0.000 claims abstract description 52
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
235000019789 appetite Nutrition 0.000 claims abstract description 6
230000036528 appetite Effects 0.000 claims abstract description 6
-1 hydroxy, benzyloxy Chemical group 0.000 claims description 106
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 68
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 55
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 49
239000003795 chemical substances by application Substances 0.000 claims description 39
150000002148 esters Chemical class 0.000 claims description 38
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical group 0.000 claims description 37
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
239000011737 fluorine Substances 0.000 claims description 31
229910052731 fluorine Inorganic materials 0.000 claims description 31
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
239000003937 drug carrier Substances 0.000 claims description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
235000012631 food intake Nutrition 0.000 claims description 11
206010020772 Hypertension Diseases 0.000 claims description 10
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
239000003472 antidiabetic agent Substances 0.000 claims description 8
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 7
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 7
230000029087 digestion Effects 0.000 claims description 7
229940126904 hypoglycaemic agent Drugs 0.000 claims description 7
230000004060 metabolic process Effects 0.000 claims description 7
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
208000032928 Dyslipidaemia Diseases 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
238000010521 absorption reaction Methods 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 6
206010012601 diabetes mellitus Diseases 0.000 claims description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
239000004744 fabric Substances 0.000 claims description 5
230000037406 food intake Effects 0.000 claims description 5
230000010243 gut motility Effects 0.000 claims description 5
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
230000004130 lipolysis Effects 0.000 claims description 5
230000036186 satiety Effects 0.000 claims description 5
235000019627 satiety Nutrition 0.000 claims description 5
230000035924 thermogenesis Effects 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
230000003143 atherosclerotic effect Effects 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
201000002859 sleep apnea Diseases 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
208000032841 Bulimia Diseases 0.000 claims description 3
206010006550 Bulimia nervosa Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
206010012335 Dependence Diseases 0.000 claims description 3
102000004877 Insulin Human genes 0.000 claims description 3
108090001061 Insulin Proteins 0.000 claims description 3
229940122199 Insulin secretagogue Drugs 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
206010036049 Polycystic ovaries Diseases 0.000 claims description 3
229940100389 Sulfonylurea Drugs 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
230000003542 behavioural effect Effects 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
208000026106 cerebrovascular disease Diseases 0.000 claims description 3
201000001883 cholelithiasis Diseases 0.000 claims description 3
230000019771 cognition Effects 0.000 claims description 3
208000010877 cognitive disease Diseases 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000003316 glycosidase inhibitor Substances 0.000 claims description 3
208000006575 hypertriglyceridemia Diseases 0.000 claims description 3
208000000509 infertility Diseases 0.000 claims description 3
231100000535 infertility Toxicity 0.000 claims description 3
230000036512 infertility Effects 0.000 claims description 3
229940125396 insulin Drugs 0.000 claims description 3
231100000551 menstrual abnormality Toxicity 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 15
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 5
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 4
239000003613 bile acid Substances 0.000 claims 4
208000015114 central nervous system disease Diseases 0.000 claims 2
230000001105 regulatory effect Effects 0.000 claims 2
GATYVSWNUQBZOD-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n'-[2-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NNC=2C(=CC=CC=2)C(F)(F)F)C=C1C1=CC=C(Cl)C=C1 GATYVSWNUQBZOD-UHFFFAOYSA-N 0.000 claims 1
BLARRMGRSJWTAH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n-piperidin-1-ylpyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NN2CCCCC2)C=C1C1=CC=C(Cl)C=C1 BLARRMGRSJWTAH-UHFFFAOYSA-N 0.000 claims 1
NTHSSZABQKWIRH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-2,4-dimethyl-n'-[4-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=C(C)C(C(=O)NNC=2C=CC(=CC=2)C(F)(F)F)=C(C)N1C1=CC=CC=C1Cl NTHSSZABQKWIRH-UHFFFAOYSA-N 0.000 claims 1
GMLVYNLULIEDNB-UHFFFAOYSA-N 2-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-n-cyclohexylpyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(N)=C(C(=O)NC2CCCCC2)C=C1C1=CC=C(Cl)C=C1 GMLVYNLULIEDNB-UHFFFAOYSA-N 0.000 claims 1
HJNXURHVMIPLQX-OFNKIYASSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n-[(1r,2s)-2-hydroxycyclohexyl]-2-methylpyrrole-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(=O)N[C@H]2[C@H](CCCC2)O)C=C1C1=CC=C(Cl)C=C1 HJNXURHVMIPLQX-OFNKIYASSA-N 0.000 claims 1
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
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