CA2303323A1 - Compounds containing six-membered rings, processes for their preparation, and their use as medicaments - Google Patents
Compounds containing six-membered rings, processes for their preparation, and their use as medicaments Download PDFInfo
- Publication number
- CA2303323A1 CA2303323A1 CA002303323A CA2303323A CA2303323A1 CA 2303323 A1 CA2303323 A1 CA 2303323A1 CA 002303323 A CA002303323 A CA 002303323A CA 2303323 A CA2303323 A CA 2303323A CA 2303323 A1 CA2303323 A1 CA 2303323A1
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- chs
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- independently
- carbon atoms
- substituted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 568
- 238000000034 method Methods 0.000 title claims abstract description 268
- 230000008569 process Effects 0.000 title description 149
- 238000002360 preparation method Methods 0.000 title description 18
- 239000003814 drug Substances 0.000 title description 16
- -1 antibodies Substances 0.000 claims abstract description 307
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 87
- 230000002378 acidificating effect Effects 0.000 claims abstract description 49
- 108010006232 Neuraminidase Proteins 0.000 claims abstract description 42
- 102000005348 Neuraminidase Human genes 0.000 claims abstract description 41
- 230000000694 effects Effects 0.000 claims abstract description 17
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 258
- 239000000203 mixture Substances 0.000 claims description 152
- 125000004432 carbon atom Chemical group C* 0.000 claims description 97
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 75
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000006239 protecting group Chemical group 0.000 claims description 44
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 150000001408 amides Chemical class 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000001727 in vivo Methods 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000002702 enteric coating Substances 0.000 claims description 16
- 238000009505 enteric coating Methods 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 15
- 125000004419 alkynylene group Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
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- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
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- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 206010022000 influenza Diseases 0.000 claims description 7
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
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- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
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- 229910006069 SO3H Inorganic materials 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
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- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 17
- 238000003556 assay Methods 0.000 abstract description 8
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- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 67
- 239000002253 acid Substances 0.000 description 65
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- 229940024606 amino acid Drugs 0.000 description 51
- 235000001014 amino acid Nutrition 0.000 description 51
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- 150000001413 amino acids Chemical class 0.000 description 47
- 108090000765 processed proteins & peptides Proteins 0.000 description 45
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 150000001412 amines Chemical class 0.000 description 40
- 229920001184 polypeptide Polymers 0.000 description 40
- 230000003213 activating effect Effects 0.000 description 37
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- 238000009472 formulation Methods 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 35
- 239000004480 active ingredient Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000003377 acid catalyst Substances 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 150000001540 azides Chemical class 0.000 description 26
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 25
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000002552 dosage form Substances 0.000 description 24
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- 238000006073 displacement reaction Methods 0.000 description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
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- 230000002163 immunogen Effects 0.000 description 18
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- 125000003277 amino group Chemical group 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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- 125000004093 cyano group Chemical group *C#N 0.000 description 16
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- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- 125000006413 ring segment Chemical group 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 15
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- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 11
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004148 unit process Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 102000027529 vitamin D receptor-like Human genes 0.000 description 1
- 108091008781 vitamin D receptor-like Proteins 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- LRDYTKPNLKOGSS-UHFFFAOYSA-N ytterbium(3+);tricyanide Chemical compound [Yb+3].N#[C-].N#[C-].N#[C-] LRDYTKPNLKOGSS-UHFFFAOYSA-N 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/62—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5930897P | 1997-09-17 | 1997-09-17 | |
US60/059,308 | 1997-09-17 | ||
US93864497A | 1997-09-26 | 1997-09-26 | |
US6019597P | 1997-09-26 | 1997-09-26 | |
US08/938,644 | 1997-09-26 | ||
US60/060,195 | 1997-09-26 | ||
PCT/US1998/019355 WO1999014185A1 (en) | 1997-09-17 | 1998-09-15 | Compounds containing six-membered rings, processes for their preparation, and their use as medicaments |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2303323A1 true CA2303323A1 (en) | 1999-03-25 |
Family
ID=27369627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002303323A Abandoned CA2303323A1 (en) | 1997-09-17 | 1998-09-15 | Compounds containing six-membered rings, processes for their preparation, and their use as medicaments |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP1015417A1 (en, 2012) |
JP (1) | JP2001516739A (en, 2012) |
KR (1) | KR20010024123A (en, 2012) |
CN (1) | CN1272105A (en, 2012) |
AR (1) | AR013960A1 (en, 2012) |
AU (1) | AU747702B2 (en, 2012) |
BR (1) | BR9812649A (en, 2012) |
CA (1) | CA2303323A1 (en, 2012) |
EA (1) | EA003989B1 (en, 2012) |
ID (1) | ID25516A (en, 2012) |
IL (1) | IL134691A0 (en, 2012) |
IN (1) | IN190983B (en, 2012) |
NZ (1) | NZ502988A (en, 2012) |
TR (1) | TR200000723T2 (en, 2012) |
WO (1) | WO1999014185A1 (en, 2012) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA9811595B (en) * | 1997-12-17 | 2000-06-19 | Biocryst Pharm Inc | Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors. |
US6518305B1 (en) | 1998-04-23 | 2003-02-11 | Abbott Laboratories | Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases |
US6455571B1 (en) | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
ES2198244T3 (es) * | 1999-06-11 | 2004-02-01 | F. Hoffmann-La Roche Ag | Procedimiento para la preparacion de inhibidor ro-64-0796 de la neuraminidasa. |
US6593314B1 (en) | 1999-10-19 | 2003-07-15 | Abbott Laboratories | Neuraminidase inhibitors |
WO2001028981A1 (en) * | 1999-10-19 | 2001-04-26 | Abbott Laboratories | 1-cyclohexene-1-carboxylic acid and 1-cyclohexene-1-carboxylates as neuraminidase inhibitors |
JP2001131144A (ja) * | 1999-11-02 | 2001-05-15 | Sagami Chem Res Center | 7−アザビシクロ[4.1.0]ヘプト−3−エン−3−カルボン酸エステル類の製造方法 |
US6403824B2 (en) * | 2000-02-22 | 2002-06-11 | Hoffmann-La Roche Inc. | Process for the preparation for 4,5-diamino shikimic acid derivatives |
AU2001252578A1 (en) * | 2000-04-25 | 2001-11-07 | Sankyo Company Limited | Preventives for influenza |
WO2002092555A1 (fr) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Derives d'acides sialiques |
US7122684B2 (en) | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
BRPI0620737A2 (pt) | 2005-12-28 | 2011-11-22 | Hoffmann La Roche | intermediário de epóxido na sìntese do tamiflu |
US8334319B2 (en) * | 2008-01-04 | 2012-12-18 | Roche Palo Alto Llc | Polymorphic forms of oseltamivir phosphate |
WO2011059994A2 (en) * | 2009-11-11 | 2011-05-19 | 3M Innovative Properties Company | Polymeric compositions and method of making and articles thereof |
DE102011117128A1 (de) | 2011-10-28 | 2013-05-02 | Christian-Albrechts-Universität Zu Kiel | Verbindungen zur Therapie der Influenza |
RU2469020C1 (ru) * | 2011-11-08 | 2012-12-10 | Александр Васильевич Иващенко | (3r,4r,5s)-5-амино-4-ациламино-3-(1-этил-пропокси)-циклогекс-1-ен-карбоновые кислоты, их эфиры и способ применения |
CN102659615B (zh) * | 2012-05-09 | 2014-05-07 | 中国药科大学 | 奥司他韦衍生物、其制备方法及其医药用途 |
RU2520836C1 (ru) * | 2013-02-27 | 2014-06-27 | Александр Васильевич Иващенко | (3r,4r,5s)-4-амино-5-(2,2-дифторацетиламино)-3-(1-этилпропокси)-циклогекс-1-енкарбоновая кислота и ее эфиры, способ их получения и применения |
RU2633085C2 (ru) * | 2014-05-20 | 2017-10-11 | Российская Федерация, от имени которой выступает Федеральное государственное казенное учреждение "Войсковая часть 68240" | Противовирусное лекарственное средство в виде капсул и способ его получения |
CN105439884A (zh) * | 2015-10-27 | 2016-03-30 | 沈阳药科大学 | 一种奥司他韦的制备方法 |
CN108047076B (zh) * | 2017-12-26 | 2020-05-08 | 杭州新博思生物医药有限公司 | 一种奥司他韦对映异构体的制备方法 |
CN110194728B (zh) * | 2019-06-19 | 2021-04-30 | 湖南华腾制药有限公司 | 磷酸奥司他韦中间体的连续化合成方法 |
WO2022022448A1 (zh) * | 2020-07-29 | 2022-02-03 | 广州市恒诺康医药科技有限公司 | 神经氨酸酶抑制剂类化合物、其药物组合物及其用途 |
CN116375595A (zh) * | 2023-03-31 | 2023-07-04 | 重庆医药高等专科学校 | 一种磷酸奥司他韦的制备方法及精制方法 |
CN117105801A (zh) * | 2023-07-24 | 2023-11-24 | 四川青木制药有限公司 | 一种奥司他韦及其磷酸盐的制备方法及其中间体 |
CN116666669B (zh) * | 2023-07-25 | 2023-10-03 | 四川大学 | VN负载的Ir团簇及其制备方法与其在催化剂中的用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ288492B6 (en) * | 1990-04-24 | 2001-06-13 | Biota Scient Management | Derivatives of alpha-D-neuraminic acid, process of their preparation, their use and pharmaceutical preparations based thereon |
WO1992006691A1 (en) * | 1990-10-19 | 1992-04-30 | Biota Scientific Management Pty. Ltd. | Anti-viral compounds that bind the active site of influenza neuramidase and display in vivo activity against orthomyxovirus and paramyxovirus |
JP3300365B2 (ja) * | 1995-02-27 | 2002-07-08 | ギリアード サイエンシーズ,インコーポレイテッド | ウイルスまたは細菌ノイラミニダーゼの新規な選択的インヒビター |
US5763483A (en) * | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
ES2173480T3 (es) * | 1996-08-23 | 2002-10-16 | Gilead Sciences Inc | Preparacion de derivados de ciclohexeno carboxilato. |
-
1998
- 1998-09-15 AU AU95694/98A patent/AU747702B2/en not_active Expired
- 1998-09-15 WO PCT/US1998/019355 patent/WO1999014185A1/en not_active Application Discontinuation
- 1998-09-15 BR BR9812649-0A patent/BR9812649A/pt not_active Application Discontinuation
- 1998-09-15 JP JP2000511738A patent/JP2001516739A/ja not_active Withdrawn
- 1998-09-15 EP EP98949356A patent/EP1015417A1/en not_active Ceased
- 1998-09-15 CN CN98809320A patent/CN1272105A/zh active Pending
- 1998-09-15 EA EA200000332A patent/EA003989B1/ru not_active IP Right Cessation
- 1998-09-15 KR KR1020007002880A patent/KR20010024123A/ko not_active Ceased
- 1998-09-15 TR TR2000/00723T patent/TR200000723T2/xx unknown
- 1998-09-15 NZ NZ502988A patent/NZ502988A/xx not_active IP Right Cessation
- 1998-09-15 ID IDW20000543A patent/ID25516A/id unknown
- 1998-09-15 IL IL13469198A patent/IL134691A0/xx not_active IP Right Cessation
- 1998-09-15 CA CA002303323A patent/CA2303323A1/en not_active Abandoned
- 1998-09-17 IN IN2791DE1998 patent/IN190983B/en unknown
- 1998-09-17 AR ARP980104638A patent/AR013960A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
EP1015417A1 (en) | 2000-07-05 |
WO1999014185A1 (en) | 1999-03-25 |
EA200000332A1 (ru) | 2000-10-30 |
ID25516A (id) | 2000-10-05 |
KR20010024123A (ko) | 2001-03-26 |
AU747702B2 (en) | 2002-05-16 |
TR200000723T2 (tr) | 2001-06-21 |
EA003989B1 (ru) | 2003-12-25 |
IN190983B (en, 2012) | 2003-09-06 |
AR013960A1 (es) | 2001-01-31 |
IL134691A0 (en) | 2001-04-30 |
AU9569498A (en) | 1999-04-05 |
BR9812649A (pt) | 2000-08-22 |
NZ502988A (en) | 2002-08-28 |
JP2001516739A (ja) | 2001-10-02 |
CN1272105A (zh) | 2000-11-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |