ZA200206221B - Amino acid derivatives and use thereof as NEP, ACE and ECE inhibitors. - Google Patents
Amino acid derivatives and use thereof as NEP, ACE and ECE inhibitors. Download PDFInfo
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- ZA200206221B ZA200206221B ZA200206221A ZA200206221A ZA200206221B ZA 200206221 B ZA200206221 B ZA 200206221B ZA 200206221 A ZA200206221 A ZA 200206221A ZA 200206221 A ZA200206221 A ZA 200206221A ZA 200206221 B ZA200206221 B ZA 200206221B
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- ZA
- South Africa
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- formula
- compound
- compounds
- pharmaceutically acceptable
- acceptable acid
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- 239000003112 inhibitor Substances 0.000 title description 9
- 150000003862 amino acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- -1 cyano, nitro, amino Chemical group 0.000 claims description 19
- 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 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- FCDJBUMHEIZGOC-ACBHZAAOSA-N (2s)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(1h-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CNC2=NC=CC=C12 FCDJBUMHEIZGOC-ACBHZAAOSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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- 239000007858 starting material Substances 0.000 claims description 4
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- RHLTYGGPIVOIQX-XTXLOEGASA-N (2s)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(5-fluoro-1h-indol-3-yl)propanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CNC2=CC=C(F)C=C12 RHLTYGGPIVOIQX-XTXLOEGASA-N 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- 231100000419 toxicity Toxicity 0.000 claims description 2
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 2
- XGJQUUGDYWNJSW-ZNIKRAEXSA-N (2s)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(5-methoxy-1h-indol-3-yl)propanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(O)=O)CC1=CNC2=CC=C(OC)C=C21 XGJQUUGDYWNJSW-ZNIKRAEXSA-N 0.000 claims 1
- VDSMHDIVRBRETF-AOMIVXANSA-N (2s)-3-(1h-indol-3-yl)-2-[[2-(5-methylsulfanyl-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]propanoic acid Chemical compound C1=CC=C2C(C[C@H](NC(=O)C(CS)C3C4=CC=C(C=C4CC3)SC)C(O)=O)=CNC2=C1 VDSMHDIVRBRETF-AOMIVXANSA-N 0.000 claims 1
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- ITAFCRHBHGSAFR-AOMIVXANSA-N (2s)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-quinolin-2-ylpropanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CC=C(C=CC=C2)C2=N1 ITAFCRHBHGSAFR-AOMIVXANSA-N 0.000 description 1
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- BPQNVNSPWLYVKD-AOMIVXANSA-N (2s)-2-[[2-(5-cyano-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C1CC2=CC(C#N)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CNC2=CC=CC=C12 BPQNVNSPWLYVKD-AOMIVXANSA-N 0.000 description 1
- CSKOMJRLLWCZKY-BBHUYCHWSA-N (2s)-2-[[2-(5-ethoxy-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@H](NC(=O)C(CS)C3C4=CC=C(C=C4CC3)OCC)C(O)=O)=CNC2=C1 CSKOMJRLLWCZKY-BBHUYCHWSA-N 0.000 description 1
- XGAXYDYJXGHUKF-MHJFOBGBSA-N (2s)-3-(1-benzothiophen-3-yl)-2-[[2-(5-bromo-2,3-dihydro-1h-inden-1-yl)-3-sulfanylpropanoyl]amino]propanoic acid Chemical compound C1CC2=CC(Br)=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CSC2=CC=CC=C12 XGAXYDYJXGHUKF-MHJFOBGBSA-N 0.000 description 1
- NEVHGNNWXYABCA-AOMIVXANSA-N (2s)-3-(1h-indol-3-yl)-2-[[3-sulfanyl-2-(1,2,3,4-tetrahydronaphthalen-1-yl)propanoyl]amino]propanoic acid Chemical compound C1CCC2=CC=CC=C2C1C(CS)C(=O)N[C@H](C(=O)O)CC1=CNC2=CC=CC=C12 NEVHGNNWXYABCA-AOMIVXANSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910003691 SiBr Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
Classifications
-
- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- 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
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0001937A FR2805259B1 (fr) | 2000-02-17 | 2000-02-17 | Nouveaux derives d'aminoacides n-mercaptoacyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200206221B true ZA200206221B (en) | 2003-08-20 |
Family
ID=8847077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200206221A ZA200206221B (en) | 2000-02-17 | 2002-08-05 | Amino acid derivatives and use thereof as NEP, ACE and ECE inhibitors. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6716852B2 (es) |
| EP (1) | EP1255757B1 (es) |
| JP (1) | JP2003523343A (es) |
| KR (1) | KR100491605B1 (es) |
| CN (1) | CN1186344C (es) |
| AR (1) | AR029468A1 (es) |
| AT (1) | ATE243210T1 (es) |
| AU (2) | AU3569801A (es) |
| BR (1) | BR0108409A (es) |
| CA (1) | CA2400537A1 (es) |
| CZ (1) | CZ20022811A3 (es) |
| DE (1) | DE60100388T2 (es) |
| DK (1) | DK1255757T3 (es) |
| EA (1) | EA005004B1 (es) |
| ES (1) | ES2202279T3 (es) |
| FR (1) | FR2805259B1 (es) |
| HK (1) | HK1050896A1 (es) |
| HU (1) | HUP0300248A3 (es) |
| MX (1) | MXPA02007973A (es) |
| NO (1) | NO323871B1 (es) |
| PL (1) | PL357243A1 (es) |
| PT (1) | PT1255757E (es) |
| SK (1) | SK11822002A3 (es) |
| WO (1) | WO2001060822A1 (es) |
| ZA (1) | ZA200206221B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823212B1 (fr) * | 2001-04-10 | 2005-12-02 | Inst Nat Sante Rech Med | Inhibiteurs de la toxine botulique de type b |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| US20100190777A1 (en) | 2007-07-17 | 2010-07-29 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| FR2931151A1 (fr) * | 2008-05-13 | 2009-11-20 | Pharmaleads Soc Par Actions Si | Nouveaux derives d'amino-acides, leur procede de preparation et leur utilisation therapeutique |
| CR20170089A (es) | 2009-04-03 | 2017-07-17 | Plexxikon Inc | Composiciones del acido propano-1--sulfonico {3-[5-(4-cloro-fenil)-1h-pirrolo [2,3-b] piridina-3-carbonil] -2,4-difluoro-fenil}-amida y el uso de las mismas |
| NZ599866A (en) | 2009-11-06 | 2014-09-26 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| MA34948B1 (fr) | 2011-02-07 | 2014-03-01 | Plexxikon Inc | Composes et procedes de modulation de kinase, et leurs indications |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2038379C (en) * | 1990-03-22 | 2002-11-05 | Norma G. Delaney | Trifluoromethyl mercaptan and mercaptoacyl derivatives and method of using same |
| IT1277736B1 (it) * | 1995-12-28 | 1997-11-12 | Zambon Spa | Derivati tiolici ad attivita' inibitrice delle metallopeptidasi |
| FR2745571B1 (fr) * | 1996-03-04 | 1998-06-19 | Inst Nat Sante Rech Med | Nouveaux derives soufres comportant une liaison amide, leur procede de preparation, leur application a titre de medicaments, et les compositions pharmaceutiques les renfermant |
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2000
- 2000-02-17 FR FR0001937A patent/FR2805259B1/fr not_active Expired - Fee Related
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2001
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- 2001-02-16 AT AT01907822T patent/ATE243210T1/de not_active IP Right Cessation
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- 2001-02-16 CA CA002400537A patent/CA2400537A1/fr not_active Abandoned
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- 2001-02-16 SK SK1182-2002A patent/SK11822002A3/sk unknown
- 2001-02-16 CZ CZ20022811A patent/CZ20022811A3/cs unknown
- 2001-02-16 PT PT01907822T patent/PT1255757E/pt unknown
- 2001-02-16 BR BR0108409-7A patent/BR0108409A/pt not_active IP Right Cessation
- 2001-02-16 EA EA200200807A patent/EA005004B1/ru not_active IP Right Cessation
- 2001-02-16 KR KR10-2002-7010552A patent/KR100491605B1/ko not_active IP Right Cessation
- 2001-02-16 MX MXPA02007973A patent/MXPA02007973A/es active IP Right Grant
- 2001-02-16 ES ES01907822T patent/ES2202279T3/es not_active Expired - Lifetime
- 2001-02-16 US US10/203,704 patent/US6716852B2/en not_active Expired - Fee Related
- 2001-02-16 JP JP2001560206A patent/JP2003523343A/ja active Pending
- 2001-02-16 HU HU0300248A patent/HUP0300248A3/hu unknown
- 2001-02-16 WO PCT/FR2001/000463 patent/WO2001060822A1/fr active IP Right Grant
- 2001-02-16 AU AU2001235698A patent/AU2001235698B2/en not_active Ceased
- 2001-02-16 PL PL01357243A patent/PL357243A1/xx not_active Application Discontinuation
- 2001-02-16 EP EP01907822A patent/EP1255757B1/fr not_active Expired - Lifetime
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2002
- 2002-08-05 ZA ZA200206221A patent/ZA200206221B/en unknown
- 2002-08-16 NO NO20023893A patent/NO323871B1/no unknown
-
2003
- 2003-04-29 HK HK03103031A patent/HK1050896A1/xx not_active IP Right Cessation
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