DE102004017930A1 - Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel - Google Patents
Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel Download PDFInfo
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- DE102004017930A1 DE102004017930A1 DE102004017930A DE102004017930A DE102004017930A1 DE 102004017930 A1 DE102004017930 A1 DE 102004017930A1 DE 102004017930 A DE102004017930 A DE 102004017930A DE 102004017930 A DE102004017930 A DE 102004017930A DE 102004017930 A1 DE102004017930 A1 DE 102004017930A1
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- Prior art keywords
- alkyl
- phenyl
- group
- mmol
- chloro
- Prior art date
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- -1 alkyne compounds Chemical class 0.000 title claims abstract description 258
- 239000003814 drug Substances 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 title claims description 59
- 239000005557 antagonist Substances 0.000 title claims description 25
- 230000000694 effects Effects 0.000 title description 7
- 238000011282 treatment Methods 0.000 claims abstract description 56
- 208000008589 Obesity Diseases 0.000 claims abstract description 44
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- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims abstract description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
- 230000003042 antagnostic effect Effects 0.000 claims abstract description 7
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 6
- 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 4
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims description 223
- 125000000217 alkyl group Chemical group 0.000 claims description 208
- 238000000034 method Methods 0.000 claims description 137
- 239000002904 solvent Substances 0.000 claims description 107
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 229910052794 bromium Inorganic materials 0.000 claims description 59
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 55
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 44
- 125000004122 cyclic group Chemical group 0.000 claims description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000004076 pyridyl group Chemical group 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 29
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 229940079593 drug Drugs 0.000 claims description 29
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 28
- 239000011737 fluorine Substances 0.000 claims description 28
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- 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 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 230000037396 body weight Effects 0.000 claims description 19
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 18
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 17
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 17
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
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- 150000002366 halogen compounds Chemical class 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 206010003246 arthritis Diseases 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 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
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
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- 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
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 230000001364 causal effect Effects 0.000 claims description 8
- 230000020595 eating behavior Effects 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 125000001041 indolyl group Chemical group 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
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
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- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
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- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 4
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
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- LULCTSFALIFISS-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[4-(1-piperidin-1-ylpropan-2-yloxy)phenyl]ethynyl]pyridine Chemical compound C=1C=C(C#CC=2N=CC(=CC=2)C=2C=CC(Cl)=CC=2)C=CC=1OC(C)CN1CCCCC1 LULCTSFALIFISS-UHFFFAOYSA-N 0.000 claims description 3
- AMRWMMRVGZANTD-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[4-(3-pyrrolidin-1-ylprop-1-ynyl)phenyl]ethynyl]pyridine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C#CC=2C=CC(=CC=2)C#CCN2CCCC2)N=C1 AMRWMMRVGZANTD-UHFFFAOYSA-N 0.000 claims description 3
- FHRZXQRKVHGZIK-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[4-[2-(4-methylpiperidin-1-yl)propoxy]phenyl]ethynyl]pyridine Chemical compound C1CC(C)CCN1C(C)COC(C=C1)=CC=C1C#CC(N=C1)=CC=C1C1=CC=C(Cl)C=C1 FHRZXQRKVHGZIK-UHFFFAOYSA-N 0.000 claims description 3
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- XORIYRTYIUZFJR-UHFFFAOYSA-N 5-[2-[5-(4-chlorophenyl)pyridin-2-yl]ethynyl]-n-(2-pyrrolidin-1-ylpropyl)pyridin-2-amine Chemical compound C1CCCN1C(C)CNC(N=C1)=CC=C1C#CC(N=C1)=CC=C1C1=CC=C(Cl)C=C1 XORIYRTYIUZFJR-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
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- 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004017930A DE102004017930A1 (de) | 2004-04-14 | 2004-04-14 | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| JP2007507709A JP2007532596A (ja) | 2004-04-14 | 2005-04-08 | Mch拮抗効果を有する新規アルキン化合物及び前記化合物を含有する薬物 |
| CA002558755A CA2558755A1 (en) | 2004-04-14 | 2005-04-08 | Novel alkyne compounds having an mch-antagonistic effect, and medicaments containing said compounds |
| EP05732062A EP1737824A2 (de) | 2004-04-14 | 2005-04-08 | Neue alkin-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
| PCT/EP2005/003686 WO2005103032A2 (de) | 2004-04-14 | 2005-04-08 | Neue alkin-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
| UY28852A UY28852A1 (es) | 2004-04-14 | 2005-04-12 | Nuevos compuestos con estructura de alquino con acción antagonista de mch y medicamentos que contienen estos compuestos |
| PE2005000401A PE20060254A1 (es) | 2004-04-14 | 2005-04-12 | Nuevos compuestos con estructura de alquino con accion antagonistas de mch y medicamentos que contienen estos compuestos |
| ARP050101439A AR048691A1 (es) | 2004-04-14 | 2005-04-13 | Compuestos con estructura de alquino con accion antagonista de mch y medicamentos que contienen estos compuestos |
| US11/105,010 US20050245529A1 (en) | 2004-04-14 | 2005-04-13 | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| TW094111701A TW200538102A (en) | 2004-04-14 | 2005-04-13 | New alkyne compounds with mch antagonistic activity and medicaments comprising these compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004017930A DE102004017930A1 (de) | 2004-04-14 | 2004-04-14 | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004017930A1 true DE102004017930A1 (de) | 2005-11-03 |
Family
ID=34964523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004017930A Withdrawn DE102004017930A1 (de) | 2004-04-14 | 2004-04-14 | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1737824A2 (https=) |
| JP (1) | JP2007532596A (https=) |
| AR (1) | AR048691A1 (https=) |
| CA (1) | CA2558755A1 (https=) |
| DE (1) | DE102004017930A1 (https=) |
| PE (1) | PE20060254A1 (https=) |
| TW (1) | TW200538102A (https=) |
| UY (1) | UY28852A1 (https=) |
| WO (1) | WO2005103032A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7452911B2 (en) | 2002-10-31 | 2008-11-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 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 |
| CN103382174A (zh) | 2006-06-23 | 2013-11-06 | 雅培制药有限公司 | 作为组胺h3受体调节物的环丙胺衍生物 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| KR20090047542A (ko) | 2006-08-25 | 2009-05-12 | 베링거 인겔하임 인터내셔날 게엠베하 | Mch 길항 활성을 갖는 신규한 피리돈 유도체 및 당해 화합물을 포함하는 의약 |
| TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2012007560A1 (en) * | 2010-07-16 | 2012-01-19 | Merz Pharma Gmbh & Co. Kgaa | Use of a cationic amphiphilic drug for the preparation of a formulation for the reduction of subcutaneous adipose tissue |
| US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| US8633182B2 (en) | 2012-05-30 | 2014-01-21 | Boehringer Ingelheim International Gmbh | Indanyloxyphenylcyclopropanecarboxylic acids |
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| AU2014368619B2 (en) | 2013-12-19 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Antibacterial 1H-indazole and 1H-indole derivatives |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| CN110088089B (zh) | 2016-10-25 | 2023-08-29 | 勃林格殷格翰国际有限公司 | 苄基氨基吡啶基环丙烷甲酸、药物组合物及其用途 |
| US10125101B2 (en) | 2016-11-28 | 2018-11-13 | Boehringer Ingelheim International Gmbh | Indanylaminopyridylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| JP7050792B2 (ja) | 2017-01-26 | 2022-04-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンジルオキシピラジニルシクロプロパンカルボン酸、その医薬組成物及び使用 |
| EP3573959B1 (en) | 2017-01-26 | 2021-07-28 | Boehringer Ingelheim International GmbH | Benzylaminopyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| CN110214135B (zh) | 2017-01-26 | 2023-02-21 | 勃林格殷格翰国际有限公司 | 茚满基氨基吡嗪基环丙烷羧酸、药物组合物及其用途 |
| CN110177773B (zh) | 2017-01-26 | 2023-08-25 | 勃林格殷格翰国际有限公司 | 苄基氨基吡啶基环丙烷羧酸、其药物组合物及其用途 |
| US10913720B2 (en) | 2017-01-26 | 2021-02-09 | Boehringer Ingelheim International Gmbh | Benzyloxypyridylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| TWI830733B (zh) * | 2018-05-11 | 2024-02-01 | 中國大陸商迪哲(江蘇)醫藥有限公司 | 環戊烷化合物 |
Family Cites Families (10)
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| 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 |
| EP1218336A2 (en) * | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| EP1285651B1 (en) * | 2000-04-28 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonists |
| JP2004516239A (ja) * | 2000-07-06 | 2004-06-03 | ニューロジェン コーポレイション | メラニン凝集ホルモン受容体リガンド |
| 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 |
| 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 |
| 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 |
-
2004
- 2004-04-14 DE DE102004017930A patent/DE102004017930A1/de not_active Withdrawn
-
2005
- 2005-04-08 WO PCT/EP2005/003686 patent/WO2005103032A2/de not_active Ceased
- 2005-04-08 EP EP05732062A patent/EP1737824A2/de not_active Withdrawn
- 2005-04-08 CA CA002558755A patent/CA2558755A1/en not_active Abandoned
- 2005-04-08 JP JP2007507709A patent/JP2007532596A/ja active Pending
- 2005-04-12 UY UY28852A patent/UY28852A1/es not_active Application Discontinuation
- 2005-04-12 PE PE2005000401A patent/PE20060254A1/es not_active Application Discontinuation
- 2005-04-13 AR ARP050101439A patent/AR048691A1/es unknown
- 2005-04-13 TW TW094111701A patent/TW200538102A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20060254A1 (es) | 2006-03-31 |
| AR048691A1 (es) | 2006-05-17 |
| UY28852A1 (es) | 2005-11-30 |
| WO2005103032A2 (de) | 2005-11-03 |
| JP2007532596A (ja) | 2007-11-15 |
| CA2558755A1 (en) | 2005-11-03 |
| TW200538102A (en) | 2005-12-01 |
| EP1737824A2 (de) | 2007-01-03 |
| WO2005103032A3 (de) | 2006-02-02 |
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