GB2392910A - 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors - Google Patents
2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors Download PDFInfo
- Publication number
- GB2392910A GB2392910A GB0315870A GB0315870A GB2392910A GB 2392910 A GB2392910 A GB 2392910A GB 0315870 A GB0315870 A GB 0315870A GB 0315870 A GB0315870 A GB 0315870A GB 2392910 A GB2392910 A GB 2392910A
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- United Kingdom
- Prior art keywords
- alkyl
- mono
- compounds
- alkoxycarbonyl
- alkoxy
- Prior art date
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- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 title abstract description 32
- 102100033174 Neutrophil elastase Human genes 0.000 title abstract description 8
- 239000003591 leukocyte elastase inhibitor Substances 0.000 title 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 206010000891 acute myocardial infarction Diseases 0.000 claims abstract description 10
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 238000011161 development Methods 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims abstract description 5
- 230000001684 chronic effect Effects 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 150000004677 hydrates Chemical class 0.000 claims abstract description 4
- 239000012453 solvate Substances 0.000 claims abstract description 4
- -1 trifluoromethylcarbonyl Chemical group 0.000 claims description 99
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 68
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 12
- 108010028275 Leukocyte Elastase Proteins 0.000 claims description 10
- 102000016799 Leukocyte elastase Human genes 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 206010019280 Heart failures Diseases 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 108091008642 NR6A Proteins 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims description 3
- 238000010490 three component reaction Methods 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 3
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- 230000002849 elastaseinhibitory effect Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 102000052502 human ELANE Human genes 0.000 abstract description 24
- 239000003112 inhibitor Substances 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 4
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- 206010007556 Cardiac failure acute Diseases 0.000 abstract description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 84
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
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- 239000000243 solution Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 235000019253 formic acid Nutrition 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- FQEIBEOBXKJAMZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=CC(C(F)(F)F)=C1 FQEIBEOBXKJAMZ-UHFFFAOYSA-N 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 125000004494 ethyl ester group Chemical group 0.000 description 10
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- RVEGSCIIXYDCJT-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CNCNC1 RVEGSCIIXYDCJT-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical class CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
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- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000010016 myocardial function Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 108010088090 pro-matrix metalloproteinase 9 Proteins 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920000685 trimethylsilyl polyphosphate Polymers 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/12—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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0315870A GB2392910A (en) | 2002-09-10 | 2003-07-07 | 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors |
ARP030103093A AR042179A1 (es) | 2002-09-10 | 2003-08-27 | Derivados de pirimidin-2 ona, procedimiento para sintetizarlos, una composicion, un procedimiento para la preparacion de la composicion y el uso de dichos compuestos para medicamentos |
KR1020057004110A KR20050042190A (ko) | 2002-09-10 | 2003-08-28 | 급성 및 만성 염증성, 허혈성 및 재형성 과정에 대한 치료제로서의 피리미디논 유도체 |
US10/527,391 US7687510B2 (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
AU2003282006A AU2003282006C1 (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory ischaemic and remodelling processes |
EP03773613.9A EP1546113B1 (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
UAA200503292A UA82074C2 (uk) | 2002-09-10 | 2003-08-28 | Похідні піримідинону як терапевтичні агенти проти гострого і хронічного запалення, ішемічних і реконструкційних процесів |
NZ538670A NZ538670A (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
PL03375647A PL375647A1 (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
MXPA05002644A MXPA05002644A (es) | 2002-09-10 | 2003-08-28 | Derivados de pirimidinona como agentes terapeuticos contra procesos de remodelacion, isquemicos e inflamatorios agudos y cronicos. |
PCT/EP2003/009525 WO2004024700A1 (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
ES03773613T ES2414865T3 (es) | 2002-09-10 | 2003-08-28 | Derivados de pirimidinona como agentes terapéuticos contra procesos inflamatorios agudos y crónicos, isquémicos y de remodelación |
CA2498051A CA2498051C (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
JP2004571738A JP4708034B2 (ja) | 2002-09-10 | 2003-08-28 | 急性および慢性炎症、虚血およびリモデリング過程に対する治療剤としてのピリミジノン誘導体 |
BR0314186-1A BR0314186A (pt) | 2002-09-10 | 2003-08-28 | Derivados de pirimidinona como agentes terapêuticos contra processos inflamatórios, isquêmicos e remodeladores, agudos e crÈnicos |
HK06108489.5A HK1088304B (en) | 2002-09-10 | 2003-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes |
UY27965A UY27965A1 (es) | 2002-09-10 | 2003-09-08 | Derivados heterocíclicos |
TW092124801A TWI314555B (en) | 2002-09-10 | 2003-09-09 | Heterocyclic derivatives |
PE2003000910A PE20041078A1 (es) | 2002-09-10 | 2003-09-09 | Derivados heterociclicos inhibidores de la elastasa leucocitica humana (elh) |
HR20050318A HRP20050318A2 (en) | 2002-09-10 | 2004-08-28 | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflamatory, ischaemic and remodelling processes |
MA28139A MA27431A1 (fr) | 2002-09-10 | 2005-03-10 | Derives de pyrimidinone utilises comme agents therapeutiques contre des processus inflammatoires ischemiques et de remodelage aigus et chroniques |
EC2005005669A ECSP055669A (es) | 2002-09-10 | 2005-03-10 | Derivados de pirimidinona como agentes terapéuticos contra procesos de remodelación, isquemicos e inflamatorios agudos y cronicos |
NO20051726A NO20051726L (no) | 2002-09-10 | 2005-04-07 | Pyrimidinonderivaer som terapeutiske midler ovenfor akutte og kroniske inflammasjons-, iskemiske og remodeleringsprosesser |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0220962A GB0220962D0 (en) | 2002-09-10 | 2002-09-10 | Heterocyclic derivatives |
GB0315870A GB2392910A (en) | 2002-09-10 | 2003-07-07 | 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
GB0315870D0 GB0315870D0 (en) | 2003-08-13 |
GB2392910A true GB2392910A (en) | 2004-03-17 |
Family
ID=39827677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB0315870A Withdrawn GB2392910A (en) | 2002-09-10 | 2003-07-07 | 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors |
Country Status (8)
Country | Link |
---|---|
JP (1) | JP4708034B2 (enrdf_load_stackoverflow) |
AR (1) | AR042179A1 (enrdf_load_stackoverflow) |
EC (1) | ECSP055669A (enrdf_load_stackoverflow) |
ES (1) | ES2414865T3 (enrdf_load_stackoverflow) |
GB (1) | GB2392910A (enrdf_load_stackoverflow) |
PE (1) | PE20041078A1 (enrdf_load_stackoverflow) |
TW (1) | TWI314555B (enrdf_load_stackoverflow) |
UA (1) | UA82074C2 (enrdf_load_stackoverflow) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008030158A1 (en) * | 2006-09-04 | 2008-03-13 | Astrazeneca Ab | Multimeric heterocyclic compounds useful as neutrophil elastase inhibitors |
US7998984B2 (en) | 2006-05-08 | 2011-08-16 | Astrazeneca Ab | 2-pyridone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial |
US8063073B2 (en) | 2003-09-18 | 2011-11-22 | Astrazeneca Ab | 2-pyridone derivatives as neutrophil elastase inhibitors and their use |
US8114881B2 (en) | 2006-05-08 | 2012-02-14 | Astrazeneca Ab | 2-pyrazinone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial |
US8232296B2 (en) | 2009-02-20 | 2012-07-31 | Astrazeneca Ab | Salt 628 |
US8436024B2 (en) | 2009-10-02 | 2013-05-07 | Astrazeneca Ab | 2-pyridone compounds |
US8466284B2 (en) | 2007-11-06 | 2013-06-18 | Astra Zeneca Ab | Some 2-pyrazinone derivatives and their use as inhibitors of neutrophile elastase |
WO2014122160A1 (en) | 2013-02-06 | 2014-08-14 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
WO2014135414A1 (en) | 2013-03-04 | 2014-09-12 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
WO2016016366A1 (en) * | 2014-07-31 | 2016-02-04 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9440930B2 (en) | 2014-07-31 | 2016-09-13 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9458113B2 (en) | 2014-07-31 | 2016-10-04 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9475779B2 (en) | 2014-07-31 | 2016-10-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
USRE47493E1 (en) | 2014-02-20 | 2019-07-09 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA03008714A (es) | 2002-09-26 | 2004-09-10 | Oreal | Polimeros secuenciados y composiciones cosmeticas que comprenden tales polimeros. |
DE60335009D1 (de) | 2002-09-26 | 2010-12-30 | Oreal | Kosmetische zusammensetzung, die einen blockpolymer und einen weichmacher enthält |
FR2860143B1 (fr) | 2003-09-26 | 2008-06-27 | Oreal | Composition cosmetique comprenant un polymere sequence et une huile siliconee non volatile |
ES2428503T3 (es) * | 2004-02-26 | 2013-11-08 | Bayer Intellectual Property Gmbh | 1,4-Diaril-dihidropirimidin-2-onas y su uso como inhibidores de elastasa de neutrófilos humanos |
US8101615B2 (en) * | 2004-02-26 | 2012-01-24 | Bayer Pharma Aktiengesellschaft | 1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors |
FR2904320B1 (fr) | 2006-07-27 | 2008-09-05 | Oreal | Polymeres sequences, et leur procede de preparation |
DE102008022521A1 (de) * | 2008-05-07 | 2009-11-12 | Bayer Schering Pharma Aktiengesellschaft | 1,4-Diaryl-pyrimidopyridazin-2,5-dione und ihre Verwendung |
HRP20120457T1 (hr) * | 2007-12-20 | 2012-06-30 | Bayer Pharma Aktiengesellschaft | 4-(4-cijano-2-tioaril)dihidropirimidinoni i njihova uporaba |
JP5480891B2 (ja) * | 2008-06-09 | 2014-04-23 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | アネレート化4−(インダゾリル)−1,4−ジヒドロピリジン誘導体およびそれらの使用方法 |
DE102009016553A1 (de) * | 2009-04-06 | 2010-10-07 | Bayer Schering Pharma Aktiengesellschaft | Sulfonamid- und Sulfoximin-substituierte Diaryldihydropyrimidinone und ihre Verwendung |
-
2003
- 2003-07-07 GB GB0315870A patent/GB2392910A/en not_active Withdrawn
- 2003-08-27 AR ARP030103093A patent/AR042179A1/es unknown
- 2003-08-28 ES ES03773613T patent/ES2414865T3/es not_active Expired - Lifetime
- 2003-08-28 JP JP2004571738A patent/JP4708034B2/ja not_active Expired - Fee Related
- 2003-08-28 UA UAA200503292A patent/UA82074C2/uk unknown
- 2003-09-09 PE PE2003000910A patent/PE20041078A1/es not_active Application Discontinuation
- 2003-09-09 TW TW092124801A patent/TWI314555B/zh not_active IP Right Cessation
-
2005
- 2005-03-10 EC EC2005005669A patent/ECSP055669A/es unknown
Non-Patent Citations (1)
Title |
---|
Journal of Combinatorial Chemistry Vol. 1, 1999, pages 105-112 * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8063073B2 (en) | 2003-09-18 | 2011-11-22 | Astrazeneca Ab | 2-pyridone derivatives as neutrophil elastase inhibitors and their use |
US8501784B2 (en) | 2003-09-18 | 2013-08-06 | Astrazeneca Ab | 2-pyridone derivatives as neutrophil elastase inhibitors and their use |
US7998984B2 (en) | 2006-05-08 | 2011-08-16 | Astrazeneca Ab | 2-pyridone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial |
US8114881B2 (en) | 2006-05-08 | 2012-02-14 | Astrazeneca Ab | 2-pyrazinone derivatives for the treatment of disease or condition in which inhibition of neutrophil elastase activity is beneficial |
WO2008030158A1 (en) * | 2006-09-04 | 2008-03-13 | Astrazeneca Ab | Multimeric heterocyclic compounds useful as neutrophil elastase inhibitors |
US8466284B2 (en) | 2007-11-06 | 2013-06-18 | Astra Zeneca Ab | Some 2-pyrazinone derivatives and their use as inhibitors of neutrophile elastase |
US8232296B2 (en) | 2009-02-20 | 2012-07-31 | Astrazeneca Ab | Salt 628 |
US8436024B2 (en) | 2009-10-02 | 2013-05-07 | Astrazeneca Ab | 2-pyridone compounds |
WO2014122160A1 (en) | 2013-02-06 | 2014-08-14 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9115093B2 (en) | 2013-03-04 | 2015-08-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
WO2014135414A1 (en) | 2013-03-04 | 2014-09-12 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
USRE47493E1 (en) | 2014-02-20 | 2019-07-09 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
WO2016016366A1 (en) * | 2014-07-31 | 2016-02-04 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9290457B2 (en) | 2014-07-31 | 2016-03-22 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9440930B2 (en) | 2014-07-31 | 2016-09-13 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9458113B2 (en) | 2014-07-31 | 2016-10-04 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9475779B2 (en) | 2014-07-31 | 2016-10-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
EP3539952A1 (en) | 2014-07-31 | 2019-09-18 | Boehringer Ingelheim International GmbH | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
EP3604308A1 (en) | 2014-07-31 | 2020-02-05 | Boehringer Ingelheim International GmbH | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
Also Published As
Publication number | Publication date |
---|---|
ES2414865T3 (es) | 2013-07-23 |
PE20041078A1 (es) | 2005-02-25 |
JP2006507355A (ja) | 2006-03-02 |
ECSP055669A (es) | 2005-05-30 |
AR042179A1 (es) | 2005-06-15 |
TWI314555B (en) | 2009-09-11 |
JP4708034B2 (ja) | 2011-06-22 |
TW200410963A (en) | 2004-07-01 |
HK1088304A1 (zh) | 2006-11-03 |
UA82074C2 (uk) | 2008-03-11 |
GB0315870D0 (en) | 2003-08-13 |
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Legal Events
Date | Code | Title | Description |
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WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |