JP2007532599A5 - - Google Patents
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- JP2007532599A5 JP2007532599A5 JP2007507719A JP2007507719A JP2007532599A5 JP 2007532599 A5 JP2007532599 A5 JP 2007532599A5 JP 2007507719 A JP2007507719 A JP 2007507719A JP 2007507719 A JP2007507719 A JP 2007507719A JP 2007532599 A5 JP2007532599 A5 JP 2007532599A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- phenyl
- cycloalkyl
- atoms
- 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.)
- Pending
Links
- -1 Alkyne compounds Chemical class 0.000 claims 44
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 11
- 125000004122 cyclic group Chemical group 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- 239000013543 active substance Substances 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 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 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 239000012467 final product Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
- 239000011630 iodine Substances 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- 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 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 1
- 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 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 206010002650 Anorexia nervosa and bulimia Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 235000021061 dietary behavior Nutrition 0.000 claims 1
- 230000000378 dietary effect Effects 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 235000006694 eating habits Nutrition 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 150000002466 imines Chemical group 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004017933A DE102004017933A1 (de) | 2004-04-14 | 2004-04-14 | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| PCT/EP2005/003710 WO2005100285A2 (de) | 2004-04-14 | 2005-04-08 | Neue alkin-verbindungen mit mch-antagonistischer wirkung und diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007532599A JP2007532599A (ja) | 2007-11-15 |
| JP2007532599A5 true JP2007532599A5 (enExample) | 2008-05-29 |
Family
ID=34982288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007507719A Pending JP2007532599A (ja) | 2004-04-14 | 2005-04-08 | Ｍｃｈ拮抗作用を示す新規アルキン化合物及び該化合物を含む医薬 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1742939A2 (enExample) |
| JP (1) | JP2007532599A (enExample) |
| CA (1) | CA2559698A1 (enExample) |
| DE (1) | DE102004017933A1 (enExample) |
| WO (1) | WO2005100285A2 (enExample) |
Families Citing this family (3)
| 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 |
| NZ575520A (en) | 2006-08-25 | 2012-03-30 | Boehringer Ingelheim Int | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
| TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7315700A (en) * | 1999-09-20 | 2001-04-24 | 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 |
-
2004
- 2004-04-14 DE DE102004017933A patent/DE102004017933A1/de not_active Withdrawn
-
2005
- 2005-04-08 JP JP2007507719A patent/JP2007532599A/ja active Pending
- 2005-04-08 EP EP05729108A patent/EP1742939A2/de not_active Withdrawn
- 2005-04-08 WO PCT/EP2005/003710 patent/WO2005100285A2/de not_active Ceased
- 2005-04-08 CA CA002559698A patent/CA2559698A1/en not_active Abandoned
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