CA2724214A1 - Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use - Google Patents
Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use Download PDFInfo
- Publication number
- CA2724214A1 CA2724214A1 CA2724214A CA2724214A CA2724214A1 CA 2724214 A1 CA2724214 A1 CA 2724214A1 CA 2724214 A CA2724214 A CA 2724214A CA 2724214 A CA2724214 A CA 2724214A CA 2724214 A1 CA2724214 A1 CA 2724214A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkyloxy
- carbonyl
- oxo
- piperazin
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 284
- -1 Alicyclic carboxylic acid derivatives Chemical class 0.000 title claims description 566
- 239000003814 drug Substances 0.000 title description 5
- 101710088194 Dehydrogenase Proteins 0.000 claims abstract description 19
- 102000004190 Enzymes Human genes 0.000 claims abstract description 12
- 108090000790 Enzymes Proteins 0.000 claims abstract description 12
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 9
- 230000006806 disease prevention Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 198
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 229910052731 fluorine Inorganic materials 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 49
- 239000000460 chlorine Substances 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000005605 benzo group Chemical group 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 14
- 125000005418 aryl aryl group Chemical group 0.000 claims description 14
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 14
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 13
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 13
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
- FIQVXCWAIJJKKB-UHFFFAOYSA-N 6-azabicyclo[3.3.1]nona-1,3,5,7-tetraene Chemical group C1=CC(C2)=NC=CC2=C1 FIQVXCWAIJJKKB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims description 3
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005939 1-azabicyclo[2.2.1]heptyl group Chemical group 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 16
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 5
- 208000032928 Dyslipidaemia Diseases 0.000 abstract description 4
- 208000008589 Obesity Diseases 0.000 abstract description 4
- 235000020824 obesity Nutrition 0.000 abstract description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 abstract description 3
- 238000001819 mass spectrum Methods 0.000 description 314
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
- 239000000243 solution Substances 0.000 description 164
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 113
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
- 239000002904 solvent Substances 0.000 description 82
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 77
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 67
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- 229940093499 ethyl acetate Drugs 0.000 description 53
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- 230000002829 reductive effect Effects 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
- 238000004128 high performance liquid chromatography Methods 0.000 description 44
- 239000012071 phase Substances 0.000 description 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
- 235000002639 sodium chloride Nutrition 0.000 description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 36
- 230000000875 corresponding effect Effects 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 33
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 33
- 239000013543 active substance Substances 0.000 description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- 239000002253 acid Substances 0.000 description 32
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 31
- 238000001816 cooling Methods 0.000 description 31
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 31
- 235000019341 magnesium sulphate Nutrition 0.000 description 31
- 239000000284 extract Substances 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
- 239000012267 brine Substances 0.000 description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 23
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 230000009467 reduction Effects 0.000 description 19
- 238000006722 reduction reaction Methods 0.000 description 19
- 102000011145 Hydroxysteroid Dehydrogenases Human genes 0.000 description 18
- 108010062875 Hydroxysteroid Dehydrogenases Proteins 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 229910052723 transition metal Inorganic materials 0.000 description 18
- 150000003624 transition metals Chemical class 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000007858 starting material Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 230000001174 ascending effect Effects 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- ACYFXXFDXDVPND-LWVQHAGNSA-N 4-[(1S,9R)-6-hydroxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carbonyl]cyclohexane-1-carboxylic acid Chemical compound C([C@@]1(C)C2=CC=CC(O)=C2C[C@@H]2C1(C)C)CN2C(=O)C1CCC(C(O)=O)CC1 ACYFXXFDXDVPND-LWVQHAGNSA-N 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
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- YGTICUOLWDVEOQ-SMNXXWJPSA-N tert-butyl (1R,9R,13S)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C1C2=CC=C(O)C=C2[C@]2(C)CCN(C(=O)OC(C)(C)C)[C@@]1([H])[C@H]2C YGTICUOLWDVEOQ-SMNXXWJPSA-N 0.000 description 1
- DDXBMIRCHRIPAJ-LAUBAEHRSA-N tert-butyl (1R,9S)-4-hydroxy-1,5,13,13-tetramethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C1C2=CC(C)=C(O)C=C2[C@@]2(C)CCN(C(=O)OC(C)(C)C)[C@]1([H])C2(C)C DDXBMIRCHRIPAJ-LAUBAEHRSA-N 0.000 description 1
- XGMDSNFMBNZRBL-LAUBAEHRSA-N tert-butyl (1R,9S)-5-hydroxy-1,4,13,13-tetramethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C1C2=CC(O)=C(C)C=C2[C@@]2(C)CCN(C(=O)OC(C)(C)C)[C@]1([H])C2(C)C XGMDSNFMBNZRBL-LAUBAEHRSA-N 0.000 description 1
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- DDXBMIRCHRIPAJ-UTKZUKDTSA-N tert-butyl (1S,9R)-4-hydroxy-1,5,13,13-tetramethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C1C2=CC(C)=C(O)C=C2[C@]2(C)CCN(C(=O)OC(C)(C)C)[C@@]1([H])C2(C)C DDXBMIRCHRIPAJ-UTKZUKDTSA-N 0.000 description 1
- QXEXQUYGXHQOHK-UTKZUKDTSA-N tert-butyl (1S,9R)-5-cyano-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C1C2=CC(C#N)=CC=C2[C@]2(C)CCN(C(=O)OC(C)(C)C)[C@@]1([H])C2(C)C QXEXQUYGXHQOHK-UTKZUKDTSA-N 0.000 description 1
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- JXDVZAPUYCOTNE-UZLBHIALSA-N tert-butyl (1S,9R)-6-amino-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC=CC(N)=C2C[C@H]2N(C(=O)OC(C)(C)C)CC[C@]1(C)C2(C)C JXDVZAPUYCOTNE-UZLBHIALSA-N 0.000 description 1
- QVTLFSLFHSCBLJ-UZLBHIALSA-N tert-butyl (1S,9R)-6-hydroxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC=CC(O)=C2C[C@H]2N(C(=O)OC(C)(C)C)CC[C@]1(C)C2(C)C QVTLFSLFHSCBLJ-UZLBHIALSA-N 0.000 description 1
- FVUKBQDYIMTYII-UHFFFAOYSA-N tert-butyl 1,13,13-trimethyl-4-(trifluoromethylsulfonyloxy)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC(OS(=O)(=O)C(F)(F)F)=CC=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C FVUKBQDYIMTYII-UHFFFAOYSA-N 0.000 description 1
- RMZQGZPAECCOKZ-UHFFFAOYSA-N tert-butyl 1,13,13-trimethyl-5-(trifluoromethylsulfonyloxy)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC=C(OS(=O)(=O)C(F)(F)F)C=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C RMZQGZPAECCOKZ-UHFFFAOYSA-N 0.000 description 1
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- CIQVIYPBUZASRE-UHFFFAOYSA-N tert-butyl 4,5-dihydroxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-10-carboxylate Chemical compound C12=CC(O)=C(O)C=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C CIQVIYPBUZASRE-UHFFFAOYSA-N 0.000 description 1
- FRXGBJNCGGOKFW-UHFFFAOYSA-N tert-butyl 4,5-dimethoxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-10-carboxylate Chemical compound C1C(C2(C)C)N(C(=O)OC(C)(C)C)CCC2(C)C2=C1C=C(OC)C(OC)=C2 FRXGBJNCGGOKFW-UHFFFAOYSA-N 0.000 description 1
- KXHAUFJDJWHHGN-UHFFFAOYSA-N tert-butyl 4-amino-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC(N)=CC=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C KXHAUFJDJWHHGN-UHFFFAOYSA-N 0.000 description 1
- IUZQHKBKVZSGII-UHFFFAOYSA-N tert-butyl 4-hydroxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC(O)=CC=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C IUZQHKBKVZSGII-UHFFFAOYSA-N 0.000 description 1
- CJRWAMMSDUQWGV-UHFFFAOYSA-N tert-butyl 4-hydroxy-5-methoxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-10-carboxylate Chemical compound C1C(C2(C)C)N(C(=O)OC(C)(C)C)CCC2(C)C2=C1C=C(OC)C(O)=C2 CJRWAMMSDUQWGV-UHFFFAOYSA-N 0.000 description 1
- JGQTWXUPZNONKH-UHFFFAOYSA-N tert-butyl 5-amino-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC=C(N)C=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C JGQTWXUPZNONKH-UHFFFAOYSA-N 0.000 description 1
- QXEXQUYGXHQOHK-UHFFFAOYSA-N tert-butyl 5-cyano-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carboxylate Chemical compound C12=CC=C(C#N)C=C2CC2N(C(=O)OC(C)(C)C)CCC1(C)C2(C)C QXEXQUYGXHQOHK-UHFFFAOYSA-N 0.000 description 1
- UZRCKGAIWRVOKA-WHHGMNPWSA-N tert-butyl N-[4-[(1S,9R)-6-hydroxy-1,13,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10-carbonyl]cyclohexyl]-N-methylcarbamate Chemical compound C1CC(N(C)C(=O)OC(C)(C)C)CCC1C(=O)N1[C@@H](C2(C)C)CC3=C(O)C=CC=C3[C@]2(C)CC1 UZRCKGAIWRVOKA-WHHGMNPWSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UNERIKIWOPRMDY-UHFFFAOYSA-N tetradeca-2,4,6-triene Chemical compound CCCCCCCC=CC=CC=CC UNERIKIWOPRMDY-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000003424 uricosuric effect Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
-
- 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
- C07D401/02—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
- C07D401/06—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 only aliphatic carbon atoms
-
- 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
- C07D401/02—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
- C07D401/08—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 alicyclic rings
-
- 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
- C07D401/02—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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08156122 | 2008-05-13 | ||
| EP08156122.7 | 2008-05-13 | ||
| PCT/EP2009/055687 WO2009138386A2 (en) | 2008-05-13 | 2009-05-12 | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
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| Publication Number | Publication Date |
|---|---|
| CA2724214A1 true CA2724214A1 (en) | 2009-11-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2724214A Abandoned CA2724214A1 (en) | 2008-05-13 | 2009-05-12 | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
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| Country | Link |
|---|---|
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| EP (1) | EP2288596B1 (enExample) |
| JP (1) | JP5711115B2 (enExample) |
| AR (1) | AR071719A1 (enExample) |
| CA (1) | CA2724214A1 (enExample) |
| CL (1) | CL2009001151A1 (enExample) |
| TW (1) | TW200950780A (enExample) |
| WO (1) | WO2009138386A2 (enExample) |
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2009
- 2009-05-12 US US12/991,722 patent/US8765780B2/en active Active
- 2009-05-12 TW TW098115741A patent/TW200950780A/zh unknown
- 2009-05-12 JP JP2011508887A patent/JP5711115B2/ja active Active
- 2009-05-12 WO PCT/EP2009/055687 patent/WO2009138386A2/en not_active Ceased
- 2009-05-12 CA CA2724214A patent/CA2724214A1/en not_active Abandoned
- 2009-05-12 EP EP09745718.8A patent/EP2288596B1/en active Active
- 2009-05-12 CL CL2009001151A patent/CL2009001151A1/es unknown
- 2009-05-12 AR ARP090101711A patent/AR071719A1/es unknown
-
2014
- 2014-02-27 US US14/191,951 patent/US9073870B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2288596A2 (en) | 2011-03-02 |
| WO2009138386A2 (en) | 2009-11-19 |
| US9073870B2 (en) | 2015-07-07 |
| US8765780B2 (en) | 2014-07-01 |
| CL2009001151A1 (es) | 2010-08-13 |
| EP2288596B1 (en) | 2016-11-30 |
| US20110269791A1 (en) | 2011-11-03 |
| WO2009138386A3 (en) | 2010-02-11 |
| AR071719A1 (es) | 2010-07-07 |
| JP2011520832A (ja) | 2011-07-21 |
| TW200950780A (en) | 2009-12-16 |
| US20140179669A1 (en) | 2014-06-26 |
| JP5711115B2 (ja) | 2015-04-30 |
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