CA2646650A1 - Inhibiteurs de l'adenylate-cyclase soluble - Google Patents
Inhibiteurs de l'adenylate-cyclase soluble Download PDFInfo
- Publication number
- CA2646650A1 CA2646650A1 CA002646650A CA2646650A CA2646650A1 CA 2646650 A1 CA2646650 A1 CA 2646650A1 CA 002646650 A CA002646650 A CA 002646650A CA 2646650 A CA2646650 A CA 2646650A CA 2646650 A1 CA2646650 A1 CA 2646650A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- acyl
- multiply
- aryl
- identically
- 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
- 108060000200 adenylate cyclase Proteins 0.000 title claims description 25
- 102000030621 adenylate cyclase Human genes 0.000 title claims description 25
- 239000003112 inhibitor Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 93
- -1 cyano, methylsulfonyl Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 16
- 229940126601 medicinal product Drugs 0.000 claims description 15
- 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 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 150000003456 sulfonamides Chemical class 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- RIRQJOXWTONIEF-UHFFFAOYSA-N CCOCl(O)(OC)OC(C)C Chemical compound CCOCl(O)(OC)OC(C)C RIRQJOXWTONIEF-UHFFFAOYSA-N 0.000 claims description 4
- JVYMKTAPCLSXLC-UHFFFAOYSA-N COClO Chemical compound COClO JVYMKTAPCLSXLC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- XELBBIVKGOHXGM-UHFFFAOYSA-N N1(CCOCC1)CCNC(=O)C=1NC2=CC=C(C=C2C1C1=CC=CC=C1)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C Chemical compound N1(CCOCC1)CCNC(=O)C=1NC2=CC=C(C=C2C1C1=CC=CC=C1)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C XELBBIVKGOHXGM-UHFFFAOYSA-N 0.000 claims description 3
- KPTQJTXCIUYIHE-UHFFFAOYSA-N O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC=CC=C1)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C Chemical compound O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC=CC=C1)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C KPTQJTXCIUYIHE-UHFFFAOYSA-N 0.000 claims description 3
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 claims description 2
- URRQFURWVJBLSS-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)sulfonylmethylamino]-3-(3-methoxyphenyl)-N-(2-morpholin-4-ylethyl)-1H-indole-2-carboxamide Chemical compound N1(CCOCC1)CCNC(=O)C=1NC2=CC=C(C=C2C1C1=CC(=CC=C1)OC)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C URRQFURWVJBLSS-UHFFFAOYSA-N 0.000 claims description 2
- NJFPKVHWDSUJBB-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)sulfonylmethylamino]-3-phenyl-N-pyridin-4-yl-1H-indole-2-carboxamide Chemical compound N1=CC=C(C=C1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC=CC=C1)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C NJFPKVHWDSUJBB-UHFFFAOYSA-N 0.000 claims description 2
- RGGFYQHXHVWJLT-UHFFFAOYSA-N O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC(=CC=C1)F)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C Chemical compound O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC(=CC=C1)F)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C RGGFYQHXHVWJLT-UHFFFAOYSA-N 0.000 claims description 2
- 230000004060 metabolic process Effects 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- LIZLFBOOCOMZAL-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)sulfonyl-(2-methoxyethyl)amino]-n-(2-morpholin-4-ylethyl)-3-phenyl-1h-indole-2-carboxamide Chemical compound C=1C=C(C(C)(C)C)C=CC=1S(=O)(=O)N(CCOC)C(C=C1C=2C=3C=CC=CC=3)=CC=C1NC=2C(=O)NCCN1CCOCC1 LIZLFBOOCOMZAL-UHFFFAOYSA-N 0.000 claims 1
- OAEAXOIQBCSFRP-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)sulfonyl-(2-methoxyethyl)amino]-n-(oxan-4-yl)-3-phenyl-1h-indole-2-carboxamide Chemical compound C=1C=C(C(C)(C)C)C=CC=1S(=O)(=O)N(CCOC)C(C=C1C=2C=3C=CC=CC=3)=CC=C1NC=2C(=O)NC1CCOCC1 OAEAXOIQBCSFRP-UHFFFAOYSA-N 0.000 claims 1
- BBWLQEZETKPMLI-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)sulfonylmethylamino]-3-(3-fluorophenyl)-N-(2-morpholin-4-ylethyl)-1H-indole-2-carboxamide Chemical compound N1(CCOCC1)CCNC(=O)C=1NC2=CC=C(C=C2C1C1=CC(=CC=C1)F)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C BBWLQEZETKPMLI-UHFFFAOYSA-N 0.000 claims 1
- WDRYJDXASDOHMS-UHFFFAOYSA-N 5-[benzyl-(4-tert-butylphenyl)sulfonylamino]-n-(2-morpholin-4-ylethyl)-3-phenyl-1h-indole-2-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N(C=1C=C2C(C=3C=CC=CC=3)=C(C(=O)NCCN3CCOCC3)NC2=CC=1)CC1=CC=CC=C1 WDRYJDXASDOHMS-UHFFFAOYSA-N 0.000 claims 1
- JJWNCLBKOSGTCH-UHFFFAOYSA-N 5-[benzyl-(4-tert-butylphenyl)sulfonylamino]-n-(oxan-4-yl)-3-phenyl-1h-indole-2-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N(C=1C=C2C(C=3C=CC=CC=3)=C(C(=O)NC3CCOCC3)NC2=CC=1)CC1=CC=CC=C1 JJWNCLBKOSGTCH-UHFFFAOYSA-N 0.000 claims 1
- AFZGALLHUARKMD-UHFFFAOYSA-N O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC(=CC=C1)OC)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C Chemical compound O1CCC(CC1)NC(=O)C=1NC2=CC=C(C=C2C=1C1=CC(=CC=C1)OC)NCS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C AFZGALLHUARKMD-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- 230000008010 sperm capacitation Effects 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 238000012360 testing method Methods 0.000 description 18
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 15
- 230000030120 acrosome reaction Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- GTSMOYLSFUBTMV-UHFFFAOYSA-N ethidium homodimer Chemical compound [H+].[H+].[Cl-].[Cl-].[Cl-].[Cl-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2C(C)=[N+]1CCCNCCNCCC[N+](C1=CC(N)=CC=C1C1=CC=C(N)C=C11)=C1C1=CC=CC=C1 GTSMOYLSFUBTMV-UHFFFAOYSA-N 0.000 description 10
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
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- 150000004820 halides Chemical class 0.000 description 3
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006014320.5 | 2006-03-23 | ||
| DE102006014320A DE102006014320B4 (de) | 2006-03-23 | 2006-03-23 | Inhibitoren der löslichen Adenylatzklase |
| PCT/EP2007/002708 WO2007107385A2 (fr) | 2006-03-23 | 2007-03-22 | Inhibiteurs de l'adénylate-cyclase soluble |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2646650A1 true CA2646650A1 (fr) | 2007-09-27 |
Family
ID=38229991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002646650A Abandoned CA2646650A1 (fr) | 2006-03-23 | 2007-03-22 | Inhibiteurs de l'adenylate-cyclase soluble |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP2001847A2 (fr) |
| JP (1) | JP2009531319A (fr) |
| KR (1) | KR20090007351A (fr) |
| CN (1) | CN101448789A (fr) |
| AR (1) | AR063661A1 (fr) |
| CA (1) | CA2646650A1 (fr) |
| DE (1) | DE102006014320B4 (fr) |
| DO (1) | DOP2007000059A (fr) |
| PE (1) | PE20080012A1 (fr) |
| TW (1) | TW200815347A (fr) |
| UY (1) | UY30236A1 (fr) |
| WO (1) | WO2007107385A2 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2036906A1 (fr) * | 2007-09-05 | 2009-03-18 | Bayer Schering Pharma Aktiengesellschaft | Azaindoles en tant qu'inhibiteurs d'adénylatcyclase soluble |
| CN108096244B (zh) * | 2018-01-25 | 2020-11-24 | 昆明医科大学 | 1-氢-2-吲哚酮-3-苄基/取代苄基-3-甲酸酯类化合物的用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442805B2 (en) * | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| CA2571881A1 (fr) * | 2004-06-22 | 2006-01-26 | Andreas P. Termin | Derives heterocycliques pour moduler les canaux calciques |
| DE102004047272A1 (de) * | 2004-09-24 | 2006-04-06 | Schering Ag | Inhibitoren der löslichen Adenylatzyklase |
-
2006
- 2006-03-23 DE DE102006014320A patent/DE102006014320B4/de not_active Expired - Fee Related
-
2007
- 2007-03-22 EP EP07723654A patent/EP2001847A2/fr not_active Withdrawn
- 2007-03-22 KR KR1020087025818A patent/KR20090007351A/ko not_active Application Discontinuation
- 2007-03-22 JP JP2009500787A patent/JP2009531319A/ja active Pending
- 2007-03-22 WO PCT/EP2007/002708 patent/WO2007107385A2/fr active Application Filing
- 2007-03-22 CA CA002646650A patent/CA2646650A1/fr not_active Abandoned
- 2007-03-22 CN CNA2007800187317A patent/CN101448789A/zh active Pending
- 2007-03-23 TW TW096110185A patent/TW200815347A/zh unknown
- 2007-03-23 PE PE2007000335A patent/PE20080012A1/es not_active Application Discontinuation
- 2007-03-23 DO DO2007000059A patent/DOP2007000059A/es unknown
- 2007-03-23 AR ARP070101194A patent/AR063661A1/es unknown
- 2007-03-23 UY UY30236A patent/UY30236A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN101448789A (zh) | 2009-06-03 |
| TW200815347A (en) | 2008-04-01 |
| EP2001847A2 (fr) | 2008-12-17 |
| KR20090007351A (ko) | 2009-01-16 |
| DOP2007000059A (es) | 2007-09-30 |
| DE102006014320B4 (de) | 2009-01-22 |
| AR063661A1 (es) | 2009-02-11 |
| WO2007107385A3 (fr) | 2007-11-29 |
| JP2009531319A (ja) | 2009-09-03 |
| WO2007107385A2 (fr) | 2007-09-27 |
| DE102006014320A1 (de) | 2007-09-27 |
| PE20080012A1 (es) | 2008-04-03 |
| UY30236A1 (es) | 2007-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |