ZA200005238B - Pyrrolidines as inhibitors of neuraminidases. - Google Patents
Pyrrolidines as inhibitors of neuraminidases. Download PDFInfo
- Publication number
- ZA200005238B ZA200005238B ZA200005238A ZA200005238A ZA200005238B ZA 200005238 B ZA200005238 B ZA 200005238B ZA 200005238 A ZA200005238 A ZA 200005238A ZA 200005238 A ZA200005238 A ZA 200005238A ZA 200005238 B ZA200005238 B ZA 200005238B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrogen
- acetamido
- pyrrolidine
- carboxylic acid
- cis
- Prior art date
Links
- 102000005348 Neuraminidase Human genes 0.000 title claims description 32
- 108010006232 Neuraminidase Proteins 0.000 title claims description 32
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000003235 pyrrolidines Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 104
- 239000001257 hydrogen Substances 0.000 claims description 101
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 241000700605 Viruses Species 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- 244000005700 microbiome Species 0.000 claims description 35
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 241000712461 unidentified influenza virus Species 0.000 claims description 26
- 206010022000 influenza Diseases 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 14
- -1 N-methylaminomethyl Chemical group 0.000 claims description 13
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 32
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 125000000262 haloalkenyl group Chemical group 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000006413 ring segment Chemical group 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 229920002554 vinyl polymer Polymers 0.000 claims 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 229910014585 C2-Ce Inorganic materials 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910018828 PO3H2 Inorganic materials 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 3
- 230000010076 replication Effects 0.000 description 3
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 3
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
- 229960003805 amantadine Drugs 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 229960000888 rimantadine Drugs 0.000 description 2
- 239000002911 sialidase inhibitor Substances 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- 241000186063 Arthrobacter Species 0.000 description 1
- 241000711404 Avian avulavirus 1 Species 0.000 description 1
- 206010006448 Bronchiolitis Diseases 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 241000712469 Fowl plague virus Species 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 241000713196 Influenza B virus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000711386 Mumps virus Species 0.000 description 1
- 241000711408 Murine respirovirus Species 0.000 description 1
- 229940123424 Neuraminidase inhibitor Drugs 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241000725643 Respiratory syncytial virus Species 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 238000012866 crystallographic experiment Methods 0.000 description 1
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 description 1
- 231100000371 dose-limiting toxicity Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical class OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- 238000002864 sequence alignment Methods 0.000 description 1
- 125000005629 sialic acid group Chemical group 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6522598A | 1998-04-23 | 1998-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200005238B true ZA200005238B (en) | 2001-12-04 |
Family
ID=22061195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200005238A ZA200005238B (en) | 1998-04-23 | 2000-09-28 | Pyrrolidines as inhibitors of neuraminidases. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1315698A1 (sk) |
| JP (1) | JP2002512224A (sk) |
| CN (1) | CN1328546A (sk) |
| AR (1) | AR018196A1 (sk) |
| AU (1) | AU3554599A (sk) |
| BG (1) | BG104962A (sk) |
| BR (1) | BR9909870A (sk) |
| CA (1) | CA2329422A1 (sk) |
| CO (1) | CO5011122A1 (sk) |
| HU (1) | HUP0101224A3 (sk) |
| IL (1) | IL138601A0 (sk) |
| NO (1) | NO20005301L (sk) |
| PL (1) | PL343678A1 (sk) |
| SK (1) | SK15092000A3 (sk) |
| TR (1) | TR200003065T2 (sk) |
| WO (1) | WO1999054299A1 (sk) |
| ZA (1) | ZA200005238B (sk) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9711095A (pt) | 1996-06-14 | 2001-07-17 | Biocryst Pharm Inc | Composto de ciclopentano substituìdo, composição e método para inibir neuraminidase de vìrus influenza e método para tratar infecção de vìrus influenza |
| AR016162A1 (es) | 1997-12-17 | 2001-06-20 | Biocryst Pharm Inc | Compuestos ciclopentano y ciclopenteno sustituidos que son de utilidad como inhibidores de la neuraminidasa y composicion que los contiene. |
| US6455571B1 (en) * | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
| AU1520300A (en) | 1998-11-05 | 2000-05-29 | Biocryst Pharmaceuticals, Inc. | New cyclopentane and cyclopentene compounds and use for detecting influenza virus |
| AU2001252578A1 (en) * | 2000-04-25 | 2001-11-07 | Sankyo Company Limited | Preventives for influenza |
| US6518299B1 (en) | 2000-10-20 | 2003-02-11 | Biocryst Pharmaceuticals, Inc. | Substituted pyrrolidine compounds useful as neuraminidase inhibitors |
| WO2002081441A1 (en) * | 2001-04-03 | 2002-10-17 | Abbott Laboratories | Process for the preparation of substituted pyrrolidine neuraminidase inhibitors |
| US20050043545A1 (en) * | 2001-11-02 | 2005-02-24 | Gianpalol Bravi | 4-(5-Membered)-heteroaryl acyl pyrrolidine derivatives as hcv inhibitors |
| US7259163B2 (en) | 2001-11-02 | 2007-08-21 | Glaxo Group Limited | 4-(6-membered)-heteroaryl acyl pyrrolidine derivatives as HCV inhibitors |
| MXPA05004435A (es) * | 2002-10-24 | 2005-07-26 | Glaxo Group Ltd | Derivados de 1-acil-pirrolidina para el tratamiento de infecciones virales. |
| CN104402754B (zh) * | 2014-11-25 | 2016-03-02 | 广东东阳光药业有限公司 | 作为神经氨酸酶抑制剂的化合物及其在药物中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4035961A1 (de) * | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE759917T1 (de) * | 1995-02-27 | 1998-10-22 | Gilead Sciences Inc | Neue selektive inhibitoren viraler oder bakterieller neuraminidasen |
| BR9711095A (pt) * | 1996-06-14 | 2001-07-17 | Biocryst Pharm Inc | Composto de ciclopentano substituìdo, composição e método para inibir neuraminidase de vìrus influenza e método para tratar infecção de vìrus influenza |
| ZA988469B (en) * | 1997-09-17 | 1999-03-17 | Biocryst Pharm Inc | Pyrrolidin-2-one compounds and their use as neuraminidase inhibitors |
-
1999
- 1999-04-12 SK SK1509-2000A patent/SK15092000A3/sk unknown
- 1999-04-12 AU AU35545/99A patent/AU3554599A/en not_active Abandoned
- 1999-04-12 CN CN99807610A patent/CN1328546A/zh active Pending
- 1999-04-12 IL IL13860199A patent/IL138601A0/xx unknown
- 1999-04-12 JP JP2000544640A patent/JP2002512224A/ja not_active Withdrawn
- 1999-04-12 CA CA002329422A patent/CA2329422A1/en not_active Abandoned
- 1999-04-12 HU HU0101224A patent/HUP0101224A3/hu unknown
- 1999-04-12 BR BR9909870-9A patent/BR9909870A/pt not_active IP Right Cessation
- 1999-04-12 TR TR2000/03065T patent/TR200003065T2/xx unknown
- 1999-04-12 WO PCT/US1999/007945 patent/WO1999054299A1/en not_active Application Discontinuation
- 1999-04-12 PL PL99343678A patent/PL343678A1/xx unknown
- 1999-04-12 EP EP99917414A patent/EP1315698A1/en not_active Withdrawn
- 1999-04-21 CO CO99024047A patent/CO5011122A1/es unknown
- 1999-04-23 AR ARP990101905A patent/AR018196A1/es not_active Application Discontinuation
-
2000
- 2000-09-28 ZA ZA200005238A patent/ZA200005238B/en unknown
- 2000-10-20 NO NO20005301A patent/NO20005301L/no not_active Application Discontinuation
- 2000-11-17 BG BG104962A patent/BG104962A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SK15092000A3 (sk) | 2001-05-10 |
| NO20005301L (no) | 2000-12-08 |
| BG104962A (bg) | 2001-07-31 |
| PL343678A1 (en) | 2001-08-27 |
| EP1315698A1 (en) | 2003-06-04 |
| HUP0101224A3 (en) | 2002-12-28 |
| CO5011122A1 (es) | 2001-02-28 |
| CA2329422A1 (en) | 1999-10-28 |
| WO1999054299A1 (en) | 1999-10-28 |
| JP2002512224A (ja) | 2002-04-23 |
| BR9909870A (pt) | 2000-12-19 |
| AR018196A1 (es) | 2001-10-31 |
| HUP0101224A2 (hu) | 2001-08-28 |
| IL138601A0 (en) | 2001-10-31 |
| TR200003065T2 (tr) | 2001-02-21 |
| CN1328546A (zh) | 2001-12-26 |
| NO20005301D0 (no) | 2000-10-20 |
| AU3554599A (en) | 1999-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200005238B (en) | Pyrrolidines as inhibitors of neuraminidases. | |
| KR101422744B1 (ko) | （１ｓ，２ｓ，３ｓ，４ｒ）－３－［（１ｓ）－１－아세틸아미노－２－에틸－부틸］－４－구아니디노－２－하이드록시－사이클로펜틸―１－카복실산 하이드레이트 및 이의 약제학적 용도 | |
| EP3177609A1 (en) | Indoles for use in influenza virus infection | |
| JP2019048898A (ja) | インフルエンザウイルスの複製の阻害剤 | |
| WO2023197791A1 (zh) | 一种环状碳酸酯核苷类化合物及其应用 | |
| WO2020241759A1 (ja) | インフルエンザウイルス感染症またはコロナウイルス感染症の予防および／または治療剤 | |
| WO2022125616A8 (en) | Dialkyl tryptamines and their therapeutic uses | |
| ZA200202060B (en) | Use of CSAIDS in rhinovirus infection. | |
| KR101494231B1 (ko) | 항바이러스 화합물 | |
| EA024618B1 (ru) | Композиция для назального применения с улучшенной стабильностью | |
| WO1995035103A1 (en) | A pharmaceutical composition for the prevention and/or treatment of viral infections and optionally inflammations as well as a method for the treatment thereof | |
| WO2007117241A1 (en) | Intramuscular antiviral treatments | |
| WO2001097804A1 (en) | Medicaments | |
| WO2001029021A1 (en) | Neuraminidase inhibitors | |
| WO2001028981A1 (en) | 1-cyclohexene-1-carboxylic acid and 1-cyclohexene-1-carboxylates as neuraminidase inhibitors | |
| CN108670965A (zh) | 特立氟胺在制备抗西尼罗病毒药物中的应用 | |
| US20230218558A1 (en) | Novel therapeutic use of pleuromutilins | |
| US20020111382A1 (en) | Antiviral compounds and method of treating viral infections | |
| RU2745265C2 (ru) | Новые составы 2-(имидазол-4-ил)-этанамида пентандиовой-1,5 кислоты для лечения и профилактики вирусных заболеваний | |
| ITMI20070093A1 (it) | Composti antivirali | |
| JPS6136728B2 (sk) | ||
| US20230151034A1 (en) | Peptidomimetic n5-methyl-n2-(nonanoyl-l-leucyl)-l-glutaminate derivatives, triazaspiro[4.14]nonadecane derivatives and similar compounds as inhibitors of norovirus and coronavirus replication | |
| WO2023201072A1 (en) | Novel 6-azauridine compounds as broad spectrum antiviral agents | |
| MX2023009961A (es) | Compuestos heterociclicos antivirales. | |
| JPH05310578A (ja) | ミゾリビンを有効成分とする感染疾患の予防または治療剤 |