ES2523864T3 - Pirimidinas antiinfecciosas y usos de las mismas - Google Patents
Pirimidinas antiinfecciosas y usos de las mismas Download PDFInfo
- Publication number
- ES2523864T3 ES2523864T3 ES11171399.6T ES11171399T ES2523864T3 ES 2523864 T3 ES2523864 T3 ES 2523864T3 ES 11171399 T ES11171399 T ES 11171399T ES 2523864 T3 ES2523864 T3 ES 2523864T3
- Authority
- ES
- Spain
- Prior art keywords
- och3
- compound
- butyl
- infective
- pyrimidines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 230000002924 anti-infective effect Effects 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- -1 3-tert-butyl-5- (2,4-dioxo-3,4-dihydropyrimidin-1 (2H) -yl) -2-methoxyphenyl Chemical group 0.000 abstract description 12
- NBRBXGKOEOGLOI-UHFFFAOYSA-N dasabuvir Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NBRBXGKOEOGLOI-UHFFFAOYSA-N 0.000 abstract 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
-
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D405/10—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 aromatic rings
-
- 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
- C07D409/10—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 aromatic rings
-
- 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
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D417/10—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 aromatic rings
-
- 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
- C07D417/14—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 three or more hetero rings
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Una forma cristalina de N-(6-(3-terc-butil-5-(2,4-dioxo-3,4-dihidropirimidin-1(2H)-il)-2-metoxifenil)naftalen- 2-il)metanosulfonamida o una forma cristalina de una sal de N-(6-(3-terc-butil-5-(2,4-dioxo- 3,4-dihidropirimidin-1(2H)-il)-2-metoxifenil)naftalen-2-il)metanosulfonamida.
Description
E11171399
13-11-2014
TABLA 1
- compuesto
- R6
- anillo/estructura anular
- sustituyente(s)
- IA-L0-2.1
- benzimidazol-2-ilo -5-N(H)S(O)2CH3
- IA-L0-2.2
- benzotiazol-2-ilo -6-N(H)S(O)2CH3
- IA-L0-2.3
- benzotiazol-2-ilo --
- IA-L0-2.4
- benzotiazol-2-ilo -5-N(H)S(O)2CH3
- IA-L0-2.5
- benzoxazol-2-ilo -6-N(H)S(O)2CH3
- IA-L0-2.6
- benzoxazol-2-ilo -6-NO2
- IA-L0-2.7
- benzoxazol-2-ilo -5-NO2
- IA-L0-2.8
- benzoxazol-2-ilo -5-N(H)S(O)2CH3
- IA-L0-2.9
- naftalen-2-ilo -6-N(H)S(O)2CH3
- IA-L0-2.10
- benzimidazol-2-ilo -5-N[S(O)2CH3]2
TABLA 2
- compuesto
- R4 R5 sustituyente(s)
- IB-L0-2.1
- -C(CH3)3 -OCH3 -H -H
- IB-L0-2.2
- -C(CH3)3 -OCH3 -OCH3
- IB-L0-2.3
- -C(CH3)3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.8
- -C(CH3)3 -H -N(H)S(O)2CH3
- IB-L0-2.14
- -C(CH3)3 -Cl -N(H)S(O)2CH3
- IB-L0-2.23
- -C(CH3)3 -OC(H)2CH3 -N(H)S(O)2CH3
- IB-L0-2.52
- -C(CH3)2C(H)2C(H)3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.53
- -OCH3 -N(H)S(O)2CH3
- IB-L0.2.54
- -C(CH3)2C(H)2OH -OCH3 -N(H)S(O)2CH3
- IB-L0-2.56
- -CF3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.57
- -I -OCH3 -N(H)S(O)2CH3
- IB-L0-2.58
- -OCH3 -N(H)S(O)2CH3
- IB-L0-2.59
- furan-2-ilo -OCH3 -N(H)S(O)2CH3
- IB-L0-2.60
- -C(F)2CF3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.61
- -OCH3 -N(H)S(O)2CH3
- IB-L0-2.64
- furan-3-ilo -OCH3 -N(H)S(O)2CH3
- IB-L0-2.66
- -C(CH3)2C(H)2OCH3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.68
- -S(O)2CH3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.69
- -Br -OCH3 -N(H)S(O)2CH3
- IB-L0-2.70
- -C(CH3)2C(O)OCH3 -OCH3 -N(H)S(O)2CH3
34
E11171399
13-11-2014
- compuesto
- R4 R5 sustituyente(s)
- IB-L0-2.71
- fenilo -OCH3 -N(H)S(O)2CH3
- IB-L0-2.72
- -C(O)OCH3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.73
- -OCH3 -N(H)S(O)2CH3
- IB-L0-2.74
- -OCH3 -N(H)S(O)2CH3
- IB-L0-2.75
- -N(H)S(O)2CH3 -OCH3 -N(H)S(O)2CH3
- IB-L0-2.76
- -OCH3 -N(R)S(O)2CH3
- IB-L0-2.77
- -C(CH3)2C(O)OH -OCH3 -N(H)S(O)2CH3
- IB-L0-2.78
- -C≡CSi(CH3)3 -OCH3 -N(H)S(O)2CH3
TABLA 3
- compuesto
- R5 sustituyente(s)
- IB-L0-2.4
- -OCH3 =NN(H)S(O)2CH3
- IB-L0-2.7
- -H =NN(H)S(O)2CH3
- IB-L0-2.9
- -OCH3 (S) -C(H)2N(H)S(O)2CH3
- IB-L0-2.10
- -OCH3 (R) -F y -C(H)2N(H)S(O)2CH3
- IB-L0-2.12
- -OCH3 -F y -C(H)2N(H)S(O)2CH3
- IB-L0-2.15
- -OCH3 (R) -C(H)2N(H)S(O)2CH3
- IB-L0-2.17
- -OCH3 -C(H)2N(H)S(O)2CH3
- IB-L0-2.20
- -OCH3 (S) -F y -C(H)2N(H)S(O)2CH3
- IB-L0-2.22
- -OCH3 (S) -C(CH3)2N(H)S(O)2CH3
- IB-L0-2.24
- -OCH3 =NN(H)C(O)OCH3
- IB-L0-2.25
- -OCH3 -CH3 y -C(H)2N(H)S(O)2CH3
- IB-L0-2.29
- -OCH3 -C(CH3)2N(H)S(O)2CH3
- IB-L0-2.31
- -OCH3 -N(H)N(H)S(O)2CH3
- IB-L0-2.34
- -OCH3 -C(O)N(H)S(O)2CH3
- IB-L0-2.36
- -OCH3 -OH
- IB-L0-2.37
- -OCH3 (R) -C(CH3)2N(H)S(O)2CH3
- IB-L0-2.44
- -OCH3 -N(H)S(O)2CH3
- IB-L0-2.50
- -OCH3 =O
35
E11171399
13-11-2014
ESQUEMA 5
5 El fenol (20-1), donde R4 es distinto de amino, se trata con una fuente de haluro electrófilo, tal como, por ejemplo, monocloruro de yodo para proporcionar el compuesto dihalogenado (20-2), donde X1 y X2 son independientemente bromo o yodo. El compuesto (20-2) se transforma en el compuesto (20-3) por medio de reacción de un agente alquilante tal como, por ejemplo, sulfato de metilo con una base tal como, por ejemplo, carbonato de potasio en acetona a reflujo. Alternativamente, yoduro de metilo en presencia de una base tal como, por ejemplo, t-butóxido de
10 potasio en un disolvente tal como, por ejemplo, tetrahidrofurano, o dimetilformamida también proporciona el compuesto (20-3). En otra alternativa más, el compuesto (20-2) se puede metilar con (trimetilsilil)diazometano en un disolvente tal como, por ejemplo, t-butil metil éter. El compuesto (20-3) se puede hacer reaccionar con uracilo, ligando (20-4), yoduro de cobre (I), y fosfato de potasio en dimetilsulfóxido de aproximadamente 40 °C a aproximadamente 100 °C para suministrar el compuesto (20-5).
15 Por ejemplo, cuando en compuesto (20-3), R4es terc-butilo, X1 es yodo, y X2 es yodo o bromo, compuesto (20-3) can be se agitó con uracilo y compuesto (20-4) en presencia de CuI y K2PO4 en DMSO durante aproximadamente 15 a aproximadamente 24 h a aproximadamente 60 °C para suministrar el compuesto (20-5). Las alternativas al ligando (20-4) para elaborar (20-5) son 8-hidroxiquinolina y 2-(2-piridil)-benzimidazol.
20
El compuesto (25-1) se puede bromar por medio de tratamiento con, por ejemplo, hidrobromuro perbromuro de
25 piridinio en un disolvente tal como, por ejemplo, ácido acético a temperatura ambiente o casi a temperatura ambiente a lo largo de un período de aproximadamente 1 a aproximadamente 8 h para producir el compuesto (25-2). El grupo amino del compuesto (25-2) se puede eliminar mediante exposición a nitrito de t-butilo en un disolvente tal como, por ejemplo, dimetilformamida a una temperatura inicialmente a temperatura ambiente y a continuación aumentar al intervalo de aproximadamente 50 a aproximadamente 65 °C para producir el compuesto (25-3). Se pueden añadir
30 alícuotas adicionales de nitrito de t-butilo a temperatura ambiente seguido de calentamiento hasta que la transformación es completa. El compuesto (25-3) se puede reducir al compuesto (25-4), por ejemplo, mediante tratamiento con hierro y cloruro de amonio.
56
Tabla CE50
- compuesto
- 1a 1b compuesto 1a 1b
- IA-LO-2,1
- D D
- IA-LO-2,2
- C B IA-LO-2,3 C C
- IA-LO-2,4
- D C IA-LO-2,5 D D
- IA-LO-2,6
- D D IA-LO-2,7 D C
- IA-LO-2,8
- C B IA-LO-2,9 A A
- IA-L0-2,10
- ND ND IB-L0-2.1 D C
- IB-L0-2.2
- D D IB-L0-2.3 A A
- IB-L0-2.4
- ND A IB-L0-2.5 B A
- IB-L0-2.6
- C B IB-L0-2.7 C B
- IB-L0-2.8
- ND B IB-L0-2.9 A A
- IB-L0-2.10
- A A IB-L0-2.11 B A
- IB-L0-2.12
- B A IB-L0-2.13 B A
- IB-L0-2.14
- C B IB-L0-2.15 C B
- IB-L0-2.16
- C A IB-L0-2.17 B A
- IB-L0-2.18
- C B IB-L0-2.19 B B
- IB-L0-2.20
- C B IB-L0-2.21 C B
- IB-L0-2.22
- C B IB-L0-2.23 C B
- IB-L0-2.24
- B B IB-L0-2.25 C B
- IB-L0-2.26
- D C IB-L0-2.27 C B
- IB-L0-2.28
- D C IB-L0-2.29 C B
- IB-L0-2.30
- C B IB-L0-2.31 C B
- IB-L0-2.32
- C B IB-LO-233 C C
- IB-L0-2.34
- D C IB-L0-2.35 D C
- IB-L0-2.36
- C B IB-L0-2.37 D C
- IB-LO-238
- D D IB-L0-2.39 D C
- IB-L0-2.40
- D C IB-L0-2.41 C C
- IB-L0-2.42
- C C IB-L0-2.43 D C
- IB-L0-2.44
- D D IB-L0-2.45 D C
- IB-L0-2.46
- ND ND IB-L0-2.47 ND ND
- IB-L0-2.48
- ND ND IB-L0-2.49 ND ND
- IB-L0-2.50
- C C IB-L0-2.51 B A
- IB-L0-2.52
- B A IB-L0-2.53 B B
- IB-L0-2.54
- B B IB-L0-2.55 B A
- IB-L0-2.56
- C A IB-L0-2.57 C B
- IB-L0-2.58
- B A IB-L0-2.59 C B
- IB-L0-2.60
- C B IB-L0-2.61 C B
- IB-L0-2.62
- C B IB-L0-2.63 C B
- IB-L0-2.64
- C A IB-L0-2.65 C B
- IB-L0-2.66
- C B IB-L0-2.67 C B
- IB-L0-2.68
- D C IB-L0-2.69 C B
- IB-L0-2.70
- D C IB-L0-2.71 C B
- IB-L0-2.72
- D C IB-L0-2.73 C C
- IB-L0-2.74
- D C IB-L0-2.75 D D
- IB-L0-2.76
- ND ND IB-L0-2.77 ND ND
- IB-L0-2.78
- ND ND IB-L0-2.79 C C
131
Claims (1)
-
imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 imagen7
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97288107P | 2007-09-17 | 2007-09-17 | |
| US972881P | 2007-09-17 | ||
| US9679208P | 2008-09-13 | 2008-09-13 | |
| US96792P | 2008-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2523864T3 true ES2523864T3 (es) | 2014-12-02 |
Family
ID=40308557
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08832330T Active ES2368879T3 (es) | 2007-09-17 | 2008-09-17 | Pirimidinas antiinfecciosas y usos de las mismas. |
| ES11171399.6T Active ES2523864T3 (es) | 2007-09-17 | 2008-09-17 | Pirimidinas antiinfecciosas y usos de las mismas |
| ES12182277.9T Active ES2592961T3 (es) | 2007-09-17 | 2008-09-17 | Pirimidinas antiinfecciosas y usos de las mismas |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08832330T Active ES2368879T3 (es) | 2007-09-17 | 2008-09-17 | Pirimidinas antiinfecciosas y usos de las mismas. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12182277.9T Active ES2592961T3 (es) | 2007-09-17 | 2008-09-17 | Pirimidinas antiinfecciosas y usos de las mismas |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US8188104B2 (es) |
| EP (3) | EP2639226B1 (es) |
| JP (3) | JP5734655B2 (es) |
| CN (4) | CN104628655A (es) |
| AT (1) | ATE519746T1 (es) |
| CA (2) | CA2699986C (es) |
| CY (3) | CY1115514T1 (es) |
| DK (3) | DK2368882T3 (es) |
| ES (3) | ES2368879T3 (es) |
| HR (2) | HRP20110809T1 (es) |
| HU (1) | HUS1500013I1 (es) |
| LT (1) | LTC2203431I2 (es) |
| LU (1) | LU92666I2 (es) |
| MX (1) | MX2010002902A (es) |
| NL (1) | NL300729I1 (es) |
| NO (1) | NO2015011I1 (es) |
| PL (3) | PL2203431T3 (es) |
| PT (3) | PT2368882E (es) |
| RU (2) | RU2539570C2 (es) |
| SI (2) | SI2368882T1 (es) |
| WO (1) | WO2009039134A1 (es) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2543620C2 (ru) | 2007-09-17 | 2015-03-10 | Эббви Бахамаз Лтд. | Производные урацила или тимина для лечения гепатита с |
| PL2203431T3 (pl) | 2007-09-17 | 2012-01-31 | Abbvie Bahamas Ltd | Pirymidyny o działaniu przeciw zakaźnym oraz ich zastosowania |
| MX2010002904A (es) | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| ES2383273T3 (es) * | 2008-07-23 | 2012-06-19 | F. Hoffmann-La Roche Ag | Compuestos heterocíclicos antivíricos |
| CA2736472A1 (en) | 2008-09-26 | 2010-04-01 | F. Hoffmann-La Roche Ag | Pyrine or pyrazine derivatives for treating hcv |
| EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| EP2389362B1 (en) | 2009-01-21 | 2019-12-11 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| WO2010111437A1 (en) * | 2009-03-25 | 2010-09-30 | Abbott Laboratories | Antiviral compounds and uses thereof |
| WO2010122082A1 (en) | 2009-04-25 | 2010-10-28 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| TWI428332B (zh) | 2009-06-09 | 2014-03-01 | Hoffmann La Roche | 雜環抗病毒化合物 |
| WO2010149598A2 (en) | 2009-06-24 | 2010-12-29 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compound |
| BR112012005616A2 (pt) | 2009-09-21 | 2016-06-21 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| KR101736218B1 (ko) | 2009-09-25 | 2017-05-16 | 오리존 지노믹스 에스.에이. | 라이신 특이적 디메틸라아제-1 억제제 및 이의 용도 |
| US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
| EP2501679A1 (en) * | 2009-11-21 | 2012-09-26 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| JP2013513628A (ja) * | 2009-12-14 | 2013-04-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | スフィンゴシンキナーゼの阻害薬 |
| WO2011073114A1 (en) * | 2009-12-14 | 2011-06-23 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| WO2011106574A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| BR122019020471B1 (pt) | 2010-04-19 | 2021-06-22 | Oryzon Genomics S.A. | Inibidores da desmetilase específica para lisina 1, seus usos e método para sua identificação, e composições farmacêuticas |
| BR112013001138A2 (pt) | 2010-07-16 | 2016-07-05 | Abbvie Inc | ligantes de fosfina para reações catalíticas |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| AU2011278927B2 (en) | 2010-07-16 | 2015-05-21 | Abbvie Ireland Unlimited Company | Process for preparing antiviral compounds |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| US9006449B2 (en) | 2010-07-29 | 2015-04-14 | Oryzon Genomics, S.A. | Cyclopropylamine derivatives useful as LSD1 inhibitors |
| WO2012013728A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Arylcyclopropylamine based demethylase inhibitors of lsd1 and their medical use |
| WO2012020725A1 (ja) * | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | Ｎｐｙ ｙ５受容体拮抗作用を有するヘテロ環誘導体 |
| WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| EP3981395A1 (en) | 2011-02-08 | 2022-04-13 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| CN102675092B (zh) * | 2011-03-14 | 2014-11-05 | 江苏中丹药物研究有限公司 | 一种制备2-芳基-2,2-二甲基乙酸甲酯的方法 |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| CN104203914B (zh) | 2011-10-20 | 2017-07-11 | 奥瑞泽恩基因组学股份有限公司 | 作为lsd1抑制剂的(杂)芳基环丙胺化合物 |
| UA116765C2 (uk) | 2011-10-20 | 2018-05-10 | Орізон Джіномікс, С.А. | (гетеро)арилциклопропіламіни як інгібітори lsd1 |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| GB2515942A (en) * | 2011-10-21 | 2015-01-07 | Abbvie Inc | Combination treatment (e.g. with ABT-072 or ABT-333) of DAAs for use in treating HCV |
| PT107894A (pt) | 2011-10-21 | 2014-10-31 | Abbvie Inc | Métodos para o tratamento de hcv compreendendo pelo menos dois agentes antivirais de actuação directa, ribavirina, mas não interferão. |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| EP2887941B1 (en) | 2012-08-21 | 2018-07-11 | AbbVie Ireland Unlimited Company | Process for preparing antiviral compounds |
| MX2015004973A (es) | 2012-10-18 | 2015-07-17 | Abbvie Inc | Formulaciones de compuestos derivados de pirimidindiona. |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| CN106065009B (zh) * | 2014-06-28 | 2019-03-01 | 广东东阳光药业有限公司 | 作为丙型肝炎抑制剂的化合物及其在药物中的应用 |
| WO2016105547A1 (en) | 2014-12-24 | 2016-06-30 | Concert Pharmaceuticals, Inc. | Deuterated dasabuvir |
| HUE055651T2 (hu) * | 2016-03-17 | 2021-12-28 | Fmc Corp | Eljárás S-enantiomer konvertálására racém formájává |
| US11192914B2 (en) | 2016-04-28 | 2021-12-07 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| WO2017202207A1 (zh) * | 2016-05-27 | 2017-11-30 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的萘环化合物及药物组合物及其应用 |
| CN110483496B (zh) * | 2019-07-17 | 2021-05-04 | 杭州市西溪医院 | 一类具有尿嘧啶-苯并噻唑结构衍生物、其制备方法及抗hcv药物的应用 |
| CN111518036A (zh) * | 2020-04-29 | 2020-08-11 | 杭州勇诚睿生物科技有限公司 | 一种达沙布韦关键中间体的制备方法 |
| US12274700B1 (en) | 2020-10-30 | 2025-04-15 | Accencio LLC | Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors |
| CN117466847A (zh) * | 2022-07-22 | 2024-01-30 | 中国医药工业研究总院有限公司 | 一种利非斯特中间体苯并呋喃-6-羧酸的制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239888A (en) | 1974-11-04 | 1980-12-16 | Pfizer Inc. | 1-Phenyluracils |
| JPS60243017A (ja) * | 1984-05-16 | 1985-12-03 | Kyowa Hakko Kogyo Co Ltd | 抗けいれん組成物 |
| AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5084084A (en) | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| ATE169915T1 (de) | 1990-02-15 | 1998-09-15 | Takeda Chemical Industries Ltd | Pyrimidindionderivate, deren herstellung und verwendung |
| NL9001075A (es) * | 1990-05-04 | 1991-12-02 | Duphar Int Res | |
| EP0489480A1 (en) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| JPH05213755A (ja) | 1992-02-07 | 1993-08-24 | Nikko Kyodo Co Ltd | 肝臓障害治療薬 |
| DE19528305A1 (de) | 1995-08-02 | 1997-02-06 | Bayer Ag | Substituierte Phenyluracile |
| US6380387B1 (en) | 1999-12-06 | 2002-04-30 | Hoffmann-La Roche Inc. | 4-Pyrimidinyl-n-acyl-l phenylalanines |
| MXPA02005564A (es) | 1999-12-06 | 2002-09-02 | Hoffmann La Roche | 4-pirimidinil-n-acil-l.fenilalaninas. |
| IL167955A (en) | 2000-02-04 | 2007-10-31 | Sumitomo Chemical Co | Inilines are converted by troiril |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| US20040002476A1 (en) * | 2002-02-14 | 2004-01-01 | Stuyver Lieven J. | Modified fluorinated nucleoside analogues |
| WO2004048343A1 (en) * | 2002-11-28 | 2004-06-10 | Schering Aktiengesellschaft | Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents |
| TW200505872A (en) * | 2003-06-13 | 2005-02-16 | Lg Life Science Ltd | Hepatitis C virus inhibitors |
| CN1829709A (zh) * | 2003-08-01 | 2006-09-06 | 健亚生物科技公司 | 对抗黄病毒的双环咪唑衍生物 |
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| EA200700243A1 (ru) * | 2004-07-14 | 2007-08-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения гепатита с |
| WO2007058392A1 (ja) * | 2005-11-21 | 2007-05-24 | Japan Tobacco Inc. | ヘテロ環化合物およびその医薬用途 |
| RU2543620C2 (ru) | 2007-09-17 | 2015-03-10 | Эббви Бахамаз Лтд. | Производные урацила или тимина для лечения гепатита с |
| MX2010002904A (es) | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| PL2203431T3 (pl) * | 2007-09-17 | 2012-01-31 | Abbvie Bahamas Ltd | Pirymidyny o działaniu przeciw zakaźnym oraz ich zastosowania |
| ES2383273T3 (es) | 2008-07-23 | 2012-06-19 | F. Hoffmann-La Roche Ag | Compuestos heterocíclicos antivíricos |
-
2008
- 2008-09-17 PL PL08832330T patent/PL2203431T3/pl unknown
- 2008-09-17 CA CA2699986A patent/CA2699986C/en not_active Expired - Fee Related
- 2008-09-17 DK DK11171399T patent/DK2368882T3/en active
- 2008-09-17 SI SI200831329T patent/SI2368882T1/sl unknown
- 2008-09-17 DK DK12182277.9T patent/DK2639226T3/en active
- 2008-09-17 ES ES08832330T patent/ES2368879T3/es active Active
- 2008-09-17 AT AT08832330T patent/ATE519746T1/de active
- 2008-09-17 PT PT11171399T patent/PT2368882E/pt unknown
- 2008-09-17 EP EP12182277.9A patent/EP2639226B1/en not_active Not-in-force
- 2008-09-17 RU RU2010114827/04A patent/RU2539570C2/ru active
- 2008-09-17 RU RU2014147354/04A patent/RU2014147354A/ru not_active Application Discontinuation
- 2008-09-17 DK DK08832330T patent/DK2203431T3/da active
- 2008-09-17 CN CN201410659529.4A patent/CN104628655A/zh active Pending
- 2008-09-17 ES ES11171399.6T patent/ES2523864T3/es active Active
- 2008-09-17 CN CN201210167588.0A patent/CN102746240B/zh not_active Expired - Fee Related
- 2008-09-17 CA CA2849420A patent/CA2849420C/en active Active
- 2008-09-17 MX MX2010002902A patent/MX2010002902A/es active IP Right Grant
- 2008-09-17 US US12/212,323 patent/US8188104B2/en active Active
- 2008-09-17 WO PCT/US2008/076592 patent/WO2009039134A1/en not_active Ceased
- 2008-09-17 EP EP20110171399 patent/EP2368882B1/en not_active Not-in-force
- 2008-09-17 EP EP20080832330 patent/EP2203431B1/en active Active
- 2008-09-17 CN CN200880113534.8A patent/CN101842360B/zh active Active
- 2008-09-17 CN CN201410657922.XA patent/CN104628654A/zh active Pending
- 2008-09-17 PT PT121822779T patent/PT2639226T/pt unknown
- 2008-09-17 ES ES12182277.9T patent/ES2592961T3/es active Active
- 2008-09-17 HR HR20110809T patent/HRP20110809T1/hr unknown
- 2008-09-17 PL PL12182277T patent/PL2639226T3/pl unknown
- 2008-09-17 PL PL11171399T patent/PL2368882T3/pl unknown
- 2008-09-17 SI SI200830433T patent/SI2203431T1/sl unknown
- 2008-09-17 JP JP2010525103A patent/JP5734655B2/ja active Active
- 2008-09-17 PT PT08832330T patent/PT2203431E/pt unknown
-
2011
- 2011-11-03 CY CY20111101065T patent/CY1115514T1/el unknown
-
2012
- 2012-04-20 US US13/451,889 patent/US8501238B2/en active Active
- 2012-10-04 JP JP2012221886A patent/JP5931683B2/ja not_active Expired - Fee Related
-
2013
- 2013-03-15 US US13/838,223 patent/US9139536B2/en active Active
-
2014
- 2014-11-12 CY CY20141100943T patent/CY1115893T1/el unknown
- 2014-11-12 HR HRP20141102 patent/HRP20141102T1/hr unknown
-
2015
- 2015-02-25 LU LU92666C patent/LU92666I2/xx unknown
- 2015-03-04 LT LTPA2015013C patent/LTC2203431I2/lt unknown
- 2015-03-17 HU HUS1500013C patent/HUS1500013I1/hu unknown
- 2015-03-26 CY CY2015013C patent/CY2015013I1/el unknown
- 2015-04-08 NL NL300729C patent/NL300729I1/nl unknown
- 2015-04-14 JP JP2015082240A patent/JP2015187106A/ja active Pending
- 2015-04-22 NO NO2015011C patent/NO2015011I1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2523864T3 (es) | Pirimidinas antiinfecciosas y usos de las mismas | |
| CO6251313A2 (es) | Proceso para la preparacion de pirazoles | |
| JP2019514863A5 (es) | ||
| Sarkar et al. | Two-fold Unsymmetrical CH Functionalization of PyrDipSi-Arenes: A General Method For Synthesis of Substituted meta-Halophenols | |
| HRP20201420T1 (hr) | Derivati žučne kiseline kao agonisti fxr/tgr5 | |
| RU2009122692A (ru) | Способ получения иматиниба и его промежуточных соединений | |
| Duan et al. | Synthesis of 2, 2′-biphenols through direct C (sp 2)–H hydroxylation of [1, 1′-biphenyl]-2-ols | |
| PE20090960A1 (es) | Derivados de quinazolinadiona, su preparacion y sus aplicaciones terapeuticas | |
| BRPI0514543A (pt) | sais de metanossulfonato de abiraterona-3-ésteres e recuperação de sais de abiraterona-3-ésteres de solução em éter de terc-butila de metila | |
| ATE368049T1 (de) | Nukleotidderivate mit einer reportergruppe und einer polymerase-enzym-blockierende gruppe | |
| HRP20050190B1 (hr) | Derivati dioksan-2-alkil karbamata, metoda njihove pripreme i primjena istih u terapeutske svrhe | |
| CO6270260A2 (es) | Metodos para producir 2`-desoxi-5-azacitidina (decitabina) | |
| PE20131086A1 (es) | Proceso para preparar compuestos antivirales | |
| PE20020616A1 (es) | Compuestos de piperidina como antagonistas del receptor ccr-3 | |
| JP2018535263A (ja) | ４−（（６−（２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−２−ヒドロキシ−３−（１ｈ−１，２，４−トリアゾール−１−イル）プロピル）ピリジン−３−イル）オキシ）ベンゾニトリル及び調製方法 | |
| PE20110147A1 (es) | Composicion y proceso - 356 | |
| Khan et al. | 6-Nitrobenzimidazole derivatives: Potential phosphodiesterase inhibitors: Synthesis and structure–activity relationship | |
| IL292090B2 (en) | Method for preparing 5-bromo-2-(3-chloro-pyridin-2-yl)-2h-pyralose-3-carboxylic acid | |
| DE602005002475D1 (de) | Verfahren zur vorbereitung von telithromycin | |
| CN104327047A (zh) | 艾菲康唑的制备方法 | |
| CN103664963A (zh) | 一种喹唑啉酮并吲唑衍生物的合成方法 | |
| CN105037236B (zh) | 瑞博西尼中间体及其制备方法 | |
| CO6551700A2 (es) | Fungicidas de azolil benceno heterobiciclico- sustituidos | |
| CN103980280A (zh) | 一种酸性条件下合成喹唑啉酮并吲唑衍生物的方法 | |
| US9453001B2 (en) | Avanafil preparation method |