ZA200501163B - Novel alkyne compounds having an MCH antagonistic effect and medicaments containing these compounds - Google Patents
Novel alkyne compounds having an MCH antagonistic effect and medicaments containing these compounds Download PDFInfo
- Publication number
- ZA200501163B ZA200501163B ZA200501163A ZA200501163A ZA200501163B ZA 200501163 B ZA200501163 B ZA 200501163B ZA 200501163 A ZA200501163 A ZA 200501163A ZA 200501163 A ZA200501163 A ZA 200501163A ZA 200501163 B ZA200501163 B ZA 200501163B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- phenyl
- chloro
- pyridin
- group
- Prior art date
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- -1 alkyne compounds Chemical class 0.000 title claims description 124
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 239000003814 drug Substances 0.000 title description 3
- 230000003042 antagnostic effect Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 130
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 125000004122 cyclic group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 24
- 208000008589 Obesity Diseases 0.000 claims description 21
- 239000013543 active substance Substances 0.000 claims description 21
- 235000020824 obesity Nutrition 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 230000037396 body weight Effects 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 239000005557 antagonist Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 150000002366 halogen compounds Chemical class 0.000 claims description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 206010003246 arthritis Diseases 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052717 sulfur 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
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000020595 eating behavior Effects 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 208000030159 metabolic disease Diseases 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 2
- 241001421185 Anomis Species 0.000 claims description 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010007882 Cellulitis Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 208000002249 Diabetes Complications Diseases 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 206010012655 Diabetic complications Diseases 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000027534 Emotional disease Diseases 0.000 claims description 2
- 208000008967 Enuresis Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 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 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 206010020710 Hyperphagia Diseases 0.000 claims description 2
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 2
- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 208000022531 anorexia 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
- 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 230000003054 hormonal effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002466 imines Chemical group 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 208000008585 mastocytosis Diseases 0.000 claims description 2
- YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical compound ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 206010029446 nocturia Diseases 0.000 claims description 2
- 208000020629 overactive bladder Diseases 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000001850 reproductive effect Effects 0.000 claims description 2
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 2
- 208000015891 sexual disease Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 230000002485 urinary effect Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- DBBVLHHZOABTAJ-UHFFFAOYSA-N 1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound CC1=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1OCCN(CC1)CCC1(O)C1=CC=CC=C1 DBBVLHHZOABTAJ-UHFFFAOYSA-N 0.000 claims 2
- RSLHENXZBQIWKW-UHFFFAOYSA-N 1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]azepane Chemical compound CC1=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1OCCN1CCCCCC1 RSLHENXZBQIWKW-UHFFFAOYSA-N 0.000 claims 2
- MZGAZQQSQTXOOZ-UHFFFAOYSA-N 1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]piperidin-3-ol Chemical compound CC1=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1OCCN1CCCC(O)C1 MZGAZQQSQTXOOZ-UHFFFAOYSA-N 0.000 claims 2
- QVALBMWKBCJVGX-UHFFFAOYSA-N 1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]piperidin-4-ol Chemical compound CC1=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1OCCN1CCC(O)CC1 QVALBMWKBCJVGX-UHFFFAOYSA-N 0.000 claims 2
- ZYBGQXVZZISJNT-UHFFFAOYSA-N 1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]phenoxy]ethyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCOC1=CC=C(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=C1 ZYBGQXVZZISJNT-UHFFFAOYSA-N 0.000 claims 2
- QRZCWTMMSJDEIF-UHFFFAOYSA-N 1-[5-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-(2-pyrrolidin-1-ylethoxy)phenyl]-n-methoxymethanimine Chemical compound CON=CC1=CC(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)=CC=C1OCCN1CCCC1 QRZCWTMMSJDEIF-UHFFFAOYSA-N 0.000 claims 2
- VJZGKOXJNFKSLL-UHFFFAOYSA-N 1-[[4-[4-[5-(4-chlorophenyl)pyridin-2-yl]but-3-ynyl]phenyl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1CCC#CC1=CC=C(C=2C=CC(Cl)=CC=2)C=N1 VJZGKOXJNFKSLL-UHFFFAOYSA-N 0.000 claims 2
- JPFIKRYNURIWOR-UHFFFAOYSA-N 2-[1-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]piperidin-4-yl]-n,n-diethylethanamine Chemical compound C1CC(CCN(CC)CC)CCN1CCOC1=CC=C(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=C1C JPFIKRYNURIWOR-UHFFFAOYSA-N 0.000 claims 2
- NROJNUSMNNXSFJ-UHFFFAOYSA-N 2-[2-[3-bromo-4-(2-pyrrolidin-1-ylethoxy)phenyl]ethynyl]-5-(4-chlorophenyl)pyridine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=C(Br)C(OCCN3CCCC3)=CC=2)N=C1 NROJNUSMNNXSFJ-UHFFFAOYSA-N 0.000 claims 2
- SFZIRKPDXXGAGC-UHFFFAOYSA-N 2-[2-[4-[2-(azetidin-1-yl)ethoxy]phenyl]ethynyl]-5-(4-chlorophenyl)pyridine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=CC(OCCN3CCC3)=CC=2)N=C1 SFZIRKPDXXGAGC-UHFFFAOYSA-N 0.000 claims 2
- CZJZYDOTIQXSRW-UHFFFAOYSA-N 2-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]phenoxy]ethyl-methylamino]ethanol Chemical compound C1=CC(OCCN(CCO)C)=CC=C1C#CC1=CC=C(C=2C=CC(Cl)=CC=2)C=N1 CZJZYDOTIQXSRW-UHFFFAOYSA-N 0.000 claims 2
- FJIXHYOXXWNORS-UHFFFAOYSA-N 2-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-1-methyl-5-(pyrrolidin-1-ylmethyl)benzimidazole Chemical compound C=1C=C2N(C)C(C#CC=3N=CC(=CC=3)C=3C=CC(Cl)=CC=3)=NC2=CC=1CN1CCCC1 FJIXHYOXXWNORS-UHFFFAOYSA-N 0.000 claims 2
- SIAMHJLSAKSXSO-UHFFFAOYSA-N 2-[[4-[4-[5-(4-chlorophenyl)pyridin-2-yl]but-3-ynyl]phenyl]methyl-methylamino]ethanol Chemical compound C1=CC(CN(CCO)C)=CC=C1CCC#CC1=CC=C(C=2C=CC(Cl)=CC=2)C=N1 SIAMHJLSAKSXSO-UHFFFAOYSA-N 0.000 claims 2
- IRFKZBKEOYHSAN-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethynyl]pyridazine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=CC(OCCN3CCCC3)=CC=2)N=N1 IRFKZBKEOYHSAN-UHFFFAOYSA-N 0.000 claims 2
- BPVSASSGWUNCSB-UHFFFAOYSA-N 3-[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl]-9-methyl-3,9-diazaspiro[5.5]undecane Chemical compound C1CN(C)CCC21CCN(CCOC=1C(=CC(=CC=1)C#CC=1N=CC(=CC=1)C=1C=CC(Cl)=CC=1)C)CC2 BPVSASSGWUNCSB-UHFFFAOYSA-N 0.000 claims 2
- WVZXSELFXMVZKK-UHFFFAOYSA-N 4-[[2-[4-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-2-methylphenoxy]ethyl-methylamino]methyl]phenol Chemical compound C=1C=C(O)C=CC=1CN(C)CCOC(C(=C1)C)=CC=C1C#CC(N=C1)=CC=C1C1=CC=C(Cl)C=C1 WVZXSELFXMVZKK-UHFFFAOYSA-N 0.000 claims 2
- UUTCYBCNOWOCAV-UHFFFAOYSA-N 4-[[4-[4-[5-(4-chlorophenyl)pyridin-2-yl]but-3-ynyl]phenyl]methyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CCCC=2C=CC(CN3CCOCC3)=CC=2)N=C1 UUTCYBCNOWOCAV-UHFFFAOYSA-N 0.000 claims 2
- CPLDSMLYXWWTHY-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-2-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]but-1-ynyl]pyridine Chemical compound C1=C(F)C(F)=CC=C1C1=CC=C(C#CCCC=2C=CC(CN3CCCC3)=CC=2)N=C1 CPLDSMLYXWWTHY-UHFFFAOYSA-N 0.000 claims 2
- JJZVJZOTKNYNRX-UHFFFAOYSA-N 5-(4-bromophenyl)-2-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]but-1-ynyl]pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C#CCCC=2C=CC(CN3CCCC3)=CC=2)N=C1 JJZVJZOTKNYNRX-UHFFFAOYSA-N 0.000 claims 2
- YYSTXGITZXTHFY-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[2-[(4-methylpiperidin-1-yl)methyl]-1-benzofuran-5-yl]ethynyl]pyridine Chemical compound C1CC(C)CCN1CC1=CC2=CC(C#CC=3N=CC(=CC=3)C=3C=CC(Cl)=CC=3)=CC=C2O1 YYSTXGITZXTHFY-UHFFFAOYSA-N 0.000 claims 2
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| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| KR20070011458A (ko) | 2004-04-08 | 2007-01-24 | 탈자진 인코포레이티드 | 키나제의 벤조트리아진 억제제 |
| 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 |
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| US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| DE102004017935A1 (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 |
| DE102004017933A1 (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 |
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| GB0413605D0 (en) | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
| PL382308A1 (pl) | 2004-08-25 | 2007-08-20 | Targegen, Inc. | Związki heterocykliczne i sposoby stosowania |
| AR051091A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| CA2580762A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
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| JP2002167382A (ja) * | 2000-07-13 | 2002-06-11 | Sankyo Co Ltd | アミノアルコ−ル誘導体 |
| GB0119474D0 (en) * | 2001-08-09 | 2001-10-03 | Astrazeneca Ab | Compounds |
| JO2311B1 (en) * | 2001-08-29 | 2005-09-12 | ميرك فروست كندا ليمتد | Alkyl inhibitors Ariel phosphodiesterase-4 |
-
2002
- 2002-10-31 DE DE10250708A patent/DE10250708A1/de not_active Ceased
-
2003
- 2003-10-25 JP JP2004547566A patent/JP4883909B2/ja not_active Expired - Fee Related
- 2003-10-25 RS YUP-2005/0331A patent/RS20050331A/sr unknown
- 2003-10-25 CN CN2003801026352A patent/CN1732154B/zh not_active Expired - Fee Related
- 2003-10-25 MX MXPA05003629A patent/MXPA05003629A/es active IP Right Grant
- 2003-10-25 KR KR1020057007667A patent/KR20050084911A/ko not_active Ceased
- 2003-10-25 EP EP10179237A patent/EP2357173A1/de not_active Withdrawn
- 2003-10-25 DK DK03809734.1T patent/DK1558578T3/da active
- 2003-10-25 ES ES03809734T patent/ES2413387T3/es not_active Expired - Lifetime
- 2003-10-25 WO PCT/EP2003/011887 patent/WO2004039780A1/de not_active Ceased
- 2003-10-25 AU AU2003300507A patent/AU2003300507B2/en not_active Ceased
- 2003-10-25 EA EA200500595A patent/EA013013B1/ru not_active IP Right Cessation
- 2003-10-25 HR HR20050384A patent/HRP20050384A2/hr not_active Application Discontinuation
- 2003-10-25 EP EP03809734A patent/EP1558578B1/de not_active Expired - Lifetime
- 2003-10-25 PL PL03376415A patent/PL376415A1/xx not_active Application Discontinuation
- 2003-10-25 BR BR0314839-4A patent/BR0314839A/pt not_active IP Right Cessation
- 2003-10-25 UA UAA200505138A patent/UA80162C2/uk unknown
- 2003-10-25 CA CA2504160A patent/CA2504160C/en not_active Expired - Fee Related
- 2003-10-29 UY UY28050A patent/UY28050A1/es not_active Application Discontinuation
- 2003-10-29 PE PE2003001091A patent/PE20040608A1/es not_active Application Discontinuation
- 2003-10-30 TW TW092130308A patent/TWI316059B/zh not_active IP Right Cessation
- 2003-10-31 AR ARP030103994A patent/AR041734A1/es unknown
-
2005
- 2005-02-09 ZA ZA200501163A patent/ZA200501163B/en unknown
- 2005-02-11 NO NO20050749A patent/NO20050749L/no not_active Application Discontinuation
- 2005-04-27 EC EC2005005764A patent/ECSP055764A/es unknown
- 2005-05-27 CO CO05052294A patent/CO5570676A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EA200500595A1 (ru) | 2005-12-29 |
| JP4883909B2 (ja) | 2012-02-22 |
| TWI316059B (en) | 2009-10-21 |
| AR041734A1 (es) | 2005-05-26 |
| EA013013B1 (ru) | 2010-02-26 |
| WO2004039780A8 (de) | 2004-07-15 |
| UY28050A1 (es) | 2004-05-31 |
| RS20050331A (sr) | 2007-11-15 |
| NO20050749L (no) | 2005-05-23 |
| DE10250708A1 (de) | 2004-05-19 |
| EP1558578B1 (de) | 2013-03-13 |
| EP2357173A1 (de) | 2011-08-17 |
| KR20050084911A (ko) | 2005-08-29 |
| PE20040608A1 (es) | 2004-10-27 |
| WO2004039780A1 (de) | 2004-05-13 |
| CA2504160A1 (en) | 2004-05-13 |
| BR0314839A (pt) | 2005-08-30 |
| TW200413346A (en) | 2004-08-01 |
| EP1558578A1 (de) | 2005-08-03 |
| MXPA05003629A (es) | 2005-09-30 |
| DK1558578T3 (da) | 2013-06-17 |
| CO5570676A2 (es) | 2005-10-31 |
| HRP20050384A2 (en) | 2006-06-30 |
| JP2006511492A (ja) | 2006-04-06 |
| AU2003300507A1 (en) | 2004-05-25 |
| CN1732154A (zh) | 2006-02-08 |
| PL376415A1 (en) | 2005-12-27 |
| CN1732154B (zh) | 2010-09-08 |
| CA2504160C (en) | 2011-12-06 |
| AU2003300507B2 (en) | 2010-12-23 |
| UA80162C2 (en) | 2007-08-27 |
| ECSP055764A (es) | 2005-07-06 |
| ES2413387T3 (es) | 2013-07-16 |
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