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
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- 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.)
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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2011
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