CA2559021A1 - Novel alkyne compounds with an mch-antagonistic action and medicaments containing said compounds - Google Patents
Novel alkyne compounds with an mch-antagonistic action and medicaments containing said compounds Download PDFInfo
- Publication number
- CA2559021A1 CA2559021A1 CA002559021A CA2559021A CA2559021A1 CA 2559021 A1 CA2559021 A1 CA 2559021A1 CA 002559021 A CA002559021 A CA 002559021A CA 2559021 A CA2559021 A CA 2559021A CA 2559021 A1 CA2559021 A1 CA 2559021A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- phenyl
- hydroxy
- cycloalkyl
- Prior art date
- 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.)
- Abandoned
Links
- -1 alkyne compounds Chemical class 0.000 title claims abstract description 242
- 150000001875 compounds Chemical class 0.000 title claims description 71
- 239000003814 drug Substances 0.000 title abstract description 7
- 230000009471 action Effects 0.000 title description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
- 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
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
- 239000013543 active substance Substances 0.000 claims description 94
- 238000000034 method Methods 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 79
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 40
- 208000008589 Obesity Diseases 0.000 claims description 39
- 235000020824 obesity Nutrition 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 32
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 31
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
- 125000004076 pyridyl group Chemical group 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
- 239000005557 antagonist Substances 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 230000037396 body weight Effects 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 150000002366 halogen compounds Chemical class 0.000 claims description 16
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 15
- 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 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 206010003246 arthritis Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 206010061428 decreased appetite Diseases 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 230000020595 eating behavior Effects 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 208000024891 symptom Diseases 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 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 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl 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
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 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
- 208000002249 Diabetes Complications Diseases 0.000 claims description 5
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 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
- 208000032841 Bulimia Diseases 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- 206010020710 Hyperphagia Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 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
- 208000027534 Emotional disease Diseases 0.000 claims description 3
- 208000008967 Enuresis Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 208000021891 Micturition disease Diseases 0.000 claims description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 3
- 238000009825 accumulation Methods 0.000 claims description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 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
- NPYCAZXPIVLLTN-UHFFFAOYSA-N n-[2-[5-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]indol-1-yl]ethyl]-n-(cyclopropylmethyl)prop-2-yn-1-amine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=C3C=CN(CCN(CC#C)CC4CC4)C3=CC=2)N=C1 NPYCAZXPIVLLTN-UHFFFAOYSA-N 0.000 claims description 3
- 206010029446 nocturia Diseases 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
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- RWLBALRSOZTGAX-UHFFFAOYSA-N n-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]-n-methylprop-2-yn-1-amine Chemical compound C1=C(C)C(OCCN(C)CC#C)=CC=C1C#CC1=CC=C(C=2C=CC(Cl)=CC=2)C=N1 RWLBALRSOZTGAX-UHFFFAOYSA-N 0.000 claims description 2
- YLIUDWWUXDQZFS-UHFFFAOYSA-N n-[[4-[2-[6-(4-chlorophenyl)quinolin-2-yl]ethynyl]phenyl]methyl]-n-methyloxan-4-amine Chemical compound C1COCCC1N(C)CC(C=C1)=CC=C1C#CC(N=C1C=C2)=CC=C1C=C2C1=CC=C(Cl)C=C1 YLIUDWWUXDQZFS-UHFFFAOYSA-N 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 47
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 abstract description 14
- 230000003042 antagnostic effect Effects 0.000 abstract description 6
- 150000001345 alkine derivatives Chemical class 0.000 abstract description 4
- 229910052796 boron Inorganic materials 0.000 abstract description 2
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 196
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
- 239000000243 solution Substances 0.000 description 101
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 100
- 235000019439 ethyl acetate Nutrition 0.000 description 98
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 93
- 239000000741 silica gel Substances 0.000 description 84
- 229910002027 silica gel Inorganic materials 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- 239000000047 product Substances 0.000 description 64
- 102400001132 Melanin-concentrating hormone Human genes 0.000 description 60
- 101800002739 Melanin-concentrating hormone Proteins 0.000 description 60
- ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 description 59
- 239000011541 reaction mixture Substances 0.000 description 50
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000012074 organic phase Substances 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000002274 desiccant Substances 0.000 description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 21
- 238000004587 chromatography analysis Methods 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- 239000004698 Polyethylene Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 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 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 230000002265 prevention Effects 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 102000029828 Melanin-concentrating hormone receptor Human genes 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
- 102000004877 Insulin Human genes 0.000 description 11
- 108090001061 Insulin Proteins 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- HVNNOHJGPWFPJS-UHFFFAOYSA-N 2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl methanesulfonate Chemical compound C1=C(OCCOS(C)(=O)=O)C(C)=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=C1 HVNNOHJGPWFPJS-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004017935A DE102004017935A1 (de) | 2004-04-14 | 2004-04-14 | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
DE102004017935.2 | 2004-04-14 | ||
PCT/EP2005/003683 WO2005103031A1 (de) | 2004-04-14 | 2005-04-08 | Neue alkin-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2559021A1 true CA2559021A1 (en) | 2005-11-03 |
Family
ID=34982358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002559021A Abandoned CA2559021A1 (en) | 2004-04-14 | 2005-04-08 | Novel alkyne compounds with an mch-antagonistic action and medicaments containing said compounds |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1740572A1 (ru) |
JP (1) | JP2007532593A (ru) |
AR (1) | AR048692A1 (ru) |
CA (1) | CA2559021A1 (ru) |
DE (1) | DE102004017935A1 (ru) |
PE (1) | PE20060333A1 (ru) |
TW (1) | TW200602025A (ru) |
UY (1) | UY28853A1 (ru) |
WO (1) | WO2005103031A1 (ru) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8618132B2 (en) | 2002-10-31 | 2013-12-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004017930A1 (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 |
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 |
EP2069327B1 (en) | 2006-08-25 | 2013-10-16 | Boehringer Ingelheim International GmbH | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
WO2008071646A1 (en) | 2006-12-11 | 2008-06-19 | Boehringer Ingelheim International Gmbh | New pyridazine derivatives with mch antagonistic activity and medicaments comprising these compounds |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5856510A (en) * | 1996-12-16 | 1999-01-05 | Allelix Biopharmaceuticals Inc. | 5-alkenyl and 5-alkynyl indole compounds |
TW544448B (en) * | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
WO2001021577A2 (en) * | 1999-09-20 | 2001-03-29 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
DE10250708A1 (de) * | 2002-10-31 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
DE102004017930A1 (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 |
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 |
-
2004
- 2004-04-14 DE DE102004017935A patent/DE102004017935A1/de not_active Withdrawn
-
2005
- 2005-04-08 CA CA002559021A patent/CA2559021A1/en not_active Abandoned
- 2005-04-08 EP EP05716558A patent/EP1740572A1/de not_active Withdrawn
- 2005-04-08 JP JP2007507706A patent/JP2007532593A/ja active Pending
- 2005-04-08 WO PCT/EP2005/003683 patent/WO2005103031A1/de not_active Application Discontinuation
- 2005-04-12 PE PE2005000400A patent/PE20060333A1/es not_active Application Discontinuation
- 2005-04-12 UY UY28853A patent/UY28853A1/es not_active Application Discontinuation
- 2005-04-13 TW TW094111717A patent/TW200602025A/zh unknown
- 2005-04-13 AR ARP050101441A patent/AR048692A1/es unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8618132B2 (en) | 2002-10-31 | 2013-12-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
Also Published As
Publication number | Publication date |
---|---|
WO2005103031A1 (de) | 2005-11-03 |
UY28853A1 (es) | 2005-11-30 |
JP2007532593A (ja) | 2007-11-15 |
AR048692A1 (es) | 2006-05-17 |
TW200602025A (en) | 2006-01-16 |
PE20060333A1 (es) | 2006-05-22 |
DE102004017935A1 (de) | 2005-11-03 |
EP1740572A1 (de) | 2007-01-10 |
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