DE102004017933A1 - Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel - Google Patents

Info

Publication number

DE102004017933A1

DE102004017933A1 DE102004017933A DE102004017933A DE102004017933A1 DE 102004017933 A1 DE102004017933 A1 DE 102004017933A1 DE 102004017933 A DE102004017933 A DE 102004017933A DE 102004017933 A DE102004017933 A DE 102004017933A DE 102004017933 A1 DE102004017933 A1 DE 102004017933A1

Authority

DE

Germany

Prior art keywords

alkyl

group

cycloalkyl

phenyl

atoms

Prior art date

2004-04-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• -1 alkyne compounds Chemical class 0.000 title claims abstract description 232
• 239000003814 drug Substances 0.000 title claims abstract description 43
• 150000001875 compounds Chemical class 0.000 title claims description 62
• 239000005557 antagonist Substances 0.000 title claims description 25
• 230000000694 effects Effects 0.000 title description 8
• 238000011282 treatment Methods 0.000 claims abstract description 56
• 208000008589 Obesity Diseases 0.000 claims abstract description 44
• 235000020824 obesity Nutrition 0.000 claims abstract description 43
• 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims abstract description 16
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
• 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 8
• 230000003042 antagnostic effect Effects 0.000 claims abstract description 6
• 206010061428 decreased appetite Diseases 0.000 claims abstract description 6
• 208000032841 Bulimia Diseases 0.000 claims abstract description 5
• 208000030814 Eating disease Diseases 0.000 claims abstract description 5
• 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
• 235000014632 disordered eating Nutrition 0.000 claims abstract description 5
• 229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
• 206010020710 Hyperphagia Diseases 0.000 claims abstract description 4
• 208000022531 anorexia Diseases 0.000 claims abstract description 4
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 4
• 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 178
• 125000004432 carbon atom Chemical group C* 0.000 claims description 83
• 239000000460 chlorine Substances 0.000 claims description 73
• 239000000203 mixture Substances 0.000 claims description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 61
• 229910052794 bromium Inorganic materials 0.000 claims description 56
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 55
• 229910052801 chlorine Inorganic materials 0.000 claims description 49
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000004122 cyclic group Chemical group 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 239000002904 solvent Substances 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
• 125000004076 pyridyl group Chemical group 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 27
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 229940079593 drug Drugs 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 239000004480 active ingredient Substances 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
• 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 19
• KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims description 19
• 230000037396 body weight Effects 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 238000011321 prophylaxis Methods 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 16
• 150000002366 halogen compounds Chemical class 0.000 claims description 16
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 229910052763 palladium Inorganic materials 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 12
• 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
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• 208000035475 disorder Diseases 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 239000012467 final product Substances 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 208000002249 Diabetes Complications Diseases 0.000 claims description 8
• 206010012655 Diabetic complications Diseases 0.000 claims description 8
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
• 206010020772 Hypertension Diseases 0.000 claims description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 230000001364 causal effect Effects 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 230000020595 eating behavior Effects 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 208000019901 Anxiety disease Diseases 0.000 claims description 7
• 230000036506 anxiety Effects 0.000 claims description 7
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 6
• 239000005977 Ethylene Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 239000000969 carrier Substances 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
• 238000001727 in vivo Methods 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 5
• 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 5
• 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 5
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 239000008103 glucose Substances 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 230000001575 pathological effect Effects 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
• 208000020401 Depressive disease Diseases 0.000 claims description 4
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
• 206010020853 Hypertonic bladder Diseases 0.000 claims description 4
• 206010027566 Micturition urgency Diseases 0.000 claims description 4
• 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 4
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• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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• 229910052760 oxygen Inorganic materials 0.000 claims description 4
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• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• ZMVNGOSUSODNRG-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[2-[(4-methylpiperidin-1-yl)methyl]-3,4-dihydro-2h-chromen-6-yl]ethynyl]pyridine Chemical compound C1CC(C)CCN1CC1OC2=CC=C(C#CC=3N=CC(=CC=3)C=3C=CC(Cl)=CC=3)C=C2CC1 ZMVNGOSUSODNRG-UHFFFAOYSA-N 0.000 claims description 3
• XKXJQYJLJAKTNF-UHFFFAOYSA-N 6-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-1-methyl-2-(pyrrolidin-1-ylmethyl)-3,4-dihydro-2h-quinoline Chemical compound C1CC2=CC(C#CC=3N=CC(=CC=3)C=3C=CC(Cl)=CC=3)=CC=C2N(C)C1CN1CCCC1 XKXJQYJLJAKTNF-UHFFFAOYSA-N 0.000 claims description 3
• YHSDVOFXUQAAAF-UHFFFAOYSA-N 6-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=C3CCC(CN4CCCC4)NC3=CC=2)N=C1 YHSDVOFXUQAAAF-UHFFFAOYSA-N 0.000 claims description 3
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