LV13074B - Fluoroalkoxy-substituted benzamides and their use as cyclic nucleotide phosphodiesterase inhibitors - Google Patents
Fluoroalkoxy-substituted benzamides and their use as cyclic nucleotide phosphodiesterase inhibitors Download PDFInfo
- Publication number
- LV13074B LV13074B LVP-03-48A LV030048A LV13074B LV 13074 B LV13074 B LV 13074B LV 030048 A LV030048 A LV 030048A LV 13074 B LV13074 B LV 13074B
- Authority
- LV
- Latvia
- Prior art keywords
- halogen
- alkoxy
- alkyl
- hydrogen
- compounds
- Prior art date
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- 229940054066 benzamide antipsychotics Drugs 0.000 title abstract 2
- 150000003936 benzamides Chemical class 0.000 title abstract 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 6
- 101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 title 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
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- -1 cyano, carboxyl Chemical group 0.000 claims description 221
- 229910052736 halogen Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 78
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 52
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000001204 N-oxides Chemical class 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- APJAEXGNDLFGPD-AWCRTANDSA-N 3-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=CC(N)=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 APJAEXGNDLFGPD-AWCRTANDSA-N 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 13
- SCEVBRBKKQZTKM-UHFFFAOYSA-N 5-[[6-chloro-5-(1-methylindol-5-yl)-1H-benzimidazol-2-yl]oxy]-N-hydroxy-2-methylbenzamide Chemical compound ClC=1C(=CC2=C(NC(=N2)OC=2C=CC(=C(C(=O)NO)C=2)C)C=1)C=1C=C2C=CN(C2=CC=1)C SCEVBRBKKQZTKM-UHFFFAOYSA-N 0.000 claims 4
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 3
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- HNBFKIZYKBBZMG-UHFFFAOYSA-N 4-(difluoromethoxy)-3-(2,2,2-trifluoroethoxy)benzaldehyde Chemical compound FC(F)OC1=CC=C(C=O)C=C1OCC(F)(F)F HNBFKIZYKBBZMG-UHFFFAOYSA-N 0.000 description 7
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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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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 2
- PRQROPMIIGLWRP-UHFFFAOYSA-N N-formyl-methionyl-leucyl-phenylalanin Chemical compound CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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Classifications
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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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199693 | 1993-07-02 |
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| LV13074B true LV13074B (en) | 2004-03-20 |
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| LVP-03-48A LV13074B (en) | 1993-07-02 | 2003-05-13 | Fluoroalkoxy-substituted benzamides and their use as cyclic nucleotide phosphodiesterase inhibitors |
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| Country | Link |
|---|---|
| US (1) | US5712298A (cs) |
| EP (1) | EP0706513B1 (cs) |
| JP (1) | JP3093271B2 (cs) |
| KR (1) | KR100331255B1 (cs) |
| CN (1) | CN1046939C (cs) |
| AT (1) | ATE217612T1 (cs) |
| AU (1) | AU687087B2 (cs) |
| CA (1) | CA2165192C (cs) |
| CY (2) | CY2389B1 (cs) |
| CZ (1) | CZ290266B6 (cs) |
| DE (2) | DE59410119D1 (cs) |
| DK (1) | DK0706513T3 (cs) |
| ES (1) | ES2176252T3 (cs) |
| FI (1) | FI112864B (cs) |
| FR (1) | FR10C0052I2 (cs) |
| HU (1) | HU220041B (cs) |
| LU (1) | LU91709I2 (cs) |
| LV (1) | LV13074B (cs) |
| NO (2) | NO305598B1 (cs) |
| NZ (1) | NZ271316A (cs) |
| PL (1) | PL178314B1 (cs) |
| PT (1) | PT706513E (cs) |
| RU (1) | RU2137754C1 (cs) |
| SG (1) | SG143011A1 (cs) |
| SI (1) | SI0706513T1 (cs) |
| SK (1) | SK283263B6 (cs) |
| WO (1) | WO1995001338A1 (cs) |
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| DE3308239A1 (de) * | 1983-03-09 | 1984-09-13 | Basf Ag, 6700 Ludwigshafen | N-acyl-anthranilsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
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| SU1512053A1 (ru) * | 1988-01-29 | 1991-01-15 | Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского | 2-Окси-3,5-дигалоид-N-[3-хлор-4-(4-галоиднафтокси-1)-фенил]-бензамиды, обладающие активностью при экспериментальном описторхозе и гименолепидозе |
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