ES2557465T3 - Moduladores de la actividad de HEC 1 y procedimientos para ello - Google Patents
Moduladores de la actividad de HEC 1 y procedimientos para ello Download PDFInfo
- Publication number
- ES2557465T3 ES2557465T3 ES11756862.6T ES11756862T ES2557465T3 ES 2557465 T3 ES2557465 T3 ES 2557465T3 ES 11756862 T ES11756862 T ES 11756862T ES 2557465 T3 ES2557465 T3 ES 2557465T3
- Authority
- ES
- Spain
- Prior art keywords
- dimethylphenyl
- mmol
- ethanone
- solution
- added
- 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
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- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 5
- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 5
- AIFVMJJGWNBKAC-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yloxy)-2,6-dimethylphenyl]-2-bromoethanone Chemical compound CC1=C(C(=O)CBr)C(C)=CC(OC=2C=C3OCOC3=CC=2)=C1 AIFVMJJGWNBKAC-UHFFFAOYSA-N 0.000 description 3
- KGGHOZLQLWWHPU-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yloxy)-2,6-dimethylphenyl]ethanone Chemical compound C1=C(C)C(C(=O)C)=C(C)C=C1OC1=CC=C(OCO2)C2=C1 KGGHOZLQLWWHPU-UHFFFAOYSA-N 0.000 description 3
- VAJGXSNETQJYTM-UHFFFAOYSA-N 1-[4-(3,5-dimethylphenoxy)-2,6-dimethylphenyl]ethanone Chemical compound C1=C(C)C(C(=O)C)=C(C)C=C1OC1=CC(C)=CC(C)=C1 VAJGXSNETQJYTM-UHFFFAOYSA-N 0.000 description 3
- HXHUHILIRBPSHX-UHFFFAOYSA-N 2-bromo-1-(4-methoxy-2,6-dimethylphenyl)ethanone Chemical compound COC1=CC(C)=C(C(=O)CBr)C(C)=C1 HXHUHILIRBPSHX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000001028 anti-proliverative effect Effects 0.000 description 3
- RKNKTACHKMTWTD-UHFFFAOYSA-N 1-(2,4,6-trimethylpyridin-3-yl)ethanone Chemical compound CC(=O)C1=C(C)C=C(C)N=C1C RKNKTACHKMTWTD-UHFFFAOYSA-N 0.000 description 2
- YTPYRGOFBLEEBD-UHFFFAOYSA-N 1-(4-chloro-2,6-dimethylphenyl)ethanone Chemical compound CC(=O)C1=C(C)C=C(Cl)C=C1C YTPYRGOFBLEEBD-UHFFFAOYSA-N 0.000 description 2
- ADQZDYLKQLQHSA-UHFFFAOYSA-N 1-[2,6-dimethyl-4-(2-methylpropoxy)phenyl]ethanone Chemical compound CC(C)COC1=CC(C)=C(C(C)=O)C(C)=C1 ADQZDYLKQLQHSA-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VYSHUFGSJJRAHL-UHFFFAOYSA-N 2-bromo-1-(2,4,6-trimethylpyridin-3-yl)ethanone;hydrobromide Chemical compound Br.CC1=CC(C)=C(C(=O)CBr)C(C)=N1 VYSHUFGSJJRAHL-UHFFFAOYSA-N 0.000 description 2
- GTAZURIDICHFSM-UHFFFAOYSA-N 2-bromo-1-[2,6-dimethyl-4-(2-methylpropoxy)phenyl]ethanone Chemical compound CC(C)COC1=CC(C)=C(C(=O)CBr)C(C)=C1 GTAZURIDICHFSM-UHFFFAOYSA-N 0.000 description 2
- KDKSUZXNKIHYII-UHFFFAOYSA-N 2-bromo-1-[4-(3,5-dimethylphenoxy)-2,6-dimethylphenyl]ethanone Chemical compound CC1=CC(C)=CC(OC=2C=C(C)C(C(=O)CBr)=C(C)C=2)=C1 KDKSUZXNKIHYII-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- SNIBQFOEOVBOKU-UHFFFAOYSA-N 4-(2,4,6-trimethylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=NC(C)=CC(C)=C1C1=CSC(N)=N1 SNIBQFOEOVBOKU-UHFFFAOYSA-N 0.000 description 2
- QGJAPSOSAWMPKU-UHFFFAOYSA-N 4-(4-methoxy-2,6-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(OC)=CC(C)=C1C1=CSC(N)=N1 QGJAPSOSAWMPKU-UHFFFAOYSA-N 0.000 description 2
- HLAPUIPSNBUWTG-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yloxy)-2,6-dimethylphenyl]-1,3-thiazol-2-amine Chemical compound CC1=CC(OC=2C=C3OCOC3=CC=2)=CC(C)=C1C1=CSC(N)=N1 HLAPUIPSNBUWTG-UHFFFAOYSA-N 0.000 description 2
- ATLRDTJFWFUUSF-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)-2,6-dimethylphenyl]-1,3-thiazol-2-amine Chemical compound C=1C(C)=C(C=2N=C(N)SC=2)C(C)=CC=1OC1=CC=C(F)C=C1 ATLRDTJFWFUUSF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 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
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- 235000019798 tripotassium phosphate Nutrition 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- UJPUGSXNZQJEPM-UHFFFAOYSA-N 1-(4-ethoxy-2,6-dimethylphenyl)ethanone Chemical compound CCOC1=CC(C)=C(C(C)=O)C(C)=C1 UJPUGSXNZQJEPM-UHFFFAOYSA-N 0.000 description 1
- LOQOGGQUEVRUSS-UHFFFAOYSA-N 1-(4-methoxy-2,6-dimethylphenyl)ethanone Chemical compound COC1=CC(C)=C(C(C)=O)C(C)=C1 LOQOGGQUEVRUSS-UHFFFAOYSA-N 0.000 description 1
- VKADWUQIQOXJPI-UHFFFAOYSA-N 2-bromo-1-(4-ethoxy-2,6-dimethylphenyl)ethanone Chemical compound CCOC1=CC(C)=C(C(=O)CBr)C(C)=C1 VKADWUQIQOXJPI-UHFFFAOYSA-N 0.000 description 1
- ZNRYPXSEYMVXGZ-UHFFFAOYSA-N 2-bromo-1-[4-(4-fluorophenoxy)-2,6-dimethylphenyl]ethanone Chemical compound CC1=C(C(=O)CBr)C(C)=CC(OC=2C=CC(F)=CC=2)=C1 ZNRYPXSEYMVXGZ-UHFFFAOYSA-N 0.000 description 1
- QTUJQDKKTJBKAU-UHFFFAOYSA-N 4-[2,6-dimethyl-4-(2-methylpropoxy)phenyl]-1,3-thiazol-2-amine Chemical compound CC1=CC(OCC(C)C)=CC(C)=C1C1=CSC(N)=N1 QTUJQDKKTJBKAU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- -1 Dimethylphenyl Chemical group 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HODDIXHTISUNRH-UHFFFAOYSA-N tert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1PC(C)(C)C HODDIXHTISUNRH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
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| PCT/US2011/028532 WO2011115998A2 (en) | 2010-03-17 | 2011-03-15 | Modulators of hec1 activity and methods therefor |
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| CN103038231B (zh) * | 2010-03-17 | 2016-04-20 | 泰纬生命科技股份有限公司 | Hec1活性调节剂及其方法 |
| CN102336720B (zh) * | 2011-03-02 | 2016-01-13 | 华中科技大学 | 2-氨基噻唑衍生物及制备方法和应用 |
| DE102011083271A1 (de) * | 2011-09-23 | 2013-03-28 | Beiersdorf Ag | Aromatische Amidothiazole, deren kosmetische oder dermatologische Verwendung sowie kosmetische oder dermatologische Zubereitungen mit einem Gehalt an solchen Aromatischen Amidothiazolen |
| CN103058949A (zh) * | 2011-10-18 | 2013-04-24 | 华东理工大学 | 做为dhodh抑制剂的噻唑衍生物及其应用 |
| US11071736B2 (en) * | 2011-11-21 | 2021-07-27 | Taivex Therapeutics Corporation | Modulators of HEC1 activity and methods therefor |
| SG10201506881PA (en) | 2011-11-21 | 2015-10-29 | Taivex Therapeutics Corp | Biomarkers for cancers responsive to modulators of hec1 activity |
| TWI640519B (zh) * | 2011-11-29 | 2018-11-11 | 泰緯生命科技股份有限公司 | Ｈｅｃ１活性調控因子及其調節方法 |
| JP6038184B2 (ja) * | 2012-02-01 | 2016-12-07 | シティ・オブ・ホープＣｉｔｙ ｏｆ Ｈｏｐｅ | リボヌクレオチドレダクターゼ阻害剤および使用方法 |
| US9422275B2 (en) | 2013-07-20 | 2016-08-23 | The Regents Of The University Of California | Small molecule modifiers of the HEC1-NEK2 interaction in G2/M |
| WO2017019772A1 (en) * | 2015-07-27 | 2017-02-02 | Sanford Burnham Prebys Medical Discovery Institute | Modulators of myocyte lipid accumulation and insulin resistance and methods of use thereof |
| US12282014B2 (en) | 2015-11-19 | 2025-04-22 | Dana-Farber Cancer Institute, Inc. | Methods of identifying compounds that interfere with ERG-driven misguidance of BAF complexes in TMPRSS2-ERG driven prostate cancers |
| EP3746124A4 (en) | 2018-01-30 | 2021-10-27 | Foghorn Therapeutics Inc. | COMPOUNDS AND THEIR USES |
| EP3758700B1 (en) * | 2018-02-28 | 2024-07-31 | University of Southern California | Compositions for modulating inflammatory and degenerative disorders |
| US12473334B2 (en) | 2018-10-17 | 2025-11-18 | Dana-Farber Cancer Institute, Inc. | SWI/SNF family chromatin remodeling complexes and uses thereof |
| US12509453B2 (en) | 2019-01-29 | 2025-12-30 | Foghorn Therapeutics Inc. | BRM/BRG1 inhibitors and uses thereof |
| US12384776B2 (en) | 2019-01-29 | 2025-08-12 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2021155264A1 (en) | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2021155262A1 (en) | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| US12383555B2 (en) | 2020-05-20 | 2025-08-12 | Foghorn Therapeutics Inc. | Methods of treating cancers |
| EP4165029B1 (en) * | 2020-06-15 | 2024-07-17 | DSM IP Assets B.V. | Process for the manufacture of alkylamidothiazoles |
| CN111925377B (zh) * | 2020-08-31 | 2022-05-31 | 上海应用技术大学 | 对位取代的二氢呋喃香豆素类神经氨酸酶抑制剂及其制备方法和应用 |
| US12606553B2 (en) | 2021-03-09 | 2026-04-21 | Foghorn Therapeutics Inc. | Crystalline forms, compositions containing same, and methods of their use |
| CN116554122B (zh) | 2023-06-29 | 2023-09-19 | 南京桦冠生物技术有限公司 | α-酮酸酰胺或取代草酸酰胺酯类化合物及其组合物 |
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| US6014A (en) * | 1849-01-09 | Stop-motion for drawing-frames | ||
| US5011A (en) * | 1847-03-13 | V boring-machine | ||
| FR2677356B1 (fr) * | 1991-06-05 | 1995-03-17 | Sanofi Sa | Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant. |
| FR2701708B1 (fr) * | 1993-02-19 | 1995-05-19 | Sanofi Elf | Dérivés de 2-amido-4-phénylthiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament. |
| CN100357283C (zh) * | 2002-04-02 | 2007-12-26 | 中国科学院上海药物研究所 | 一类甲硫氨酰氨肽酶抑制剂 |
| EP1519736A2 (en) | 2002-06-12 | 2005-04-06 | Max-Planck-Gesellschaft Zur Förderung Der Wissenschaften E.V. | Use of hec1 antagonists in the treatment of proliferative disorders and cancer |
| AU2003299378A1 (en) | 2002-10-11 | 2004-05-04 | Board Of Regents, The University Of Texas System | Method and compounds for inhibiting hec1 activity for the treatment of proliferative diseases |
| FR2854158B1 (fr) * | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| US7973169B2 (en) * | 2003-09-06 | 2011-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| FR2872813B1 (fr) | 2004-07-09 | 2007-01-19 | Sanofi Synthelabo | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| CN101048158A (zh) * | 2004-08-13 | 2007-10-03 | 健泰科生物技术公司 | 利用atp的酶的噻唑－类抑制剂 |
| AU2006244203B2 (en) * | 2005-05-09 | 2012-05-03 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
| JP4612487B2 (ja) * | 2005-06-30 | 2011-01-12 | キョーラク株式会社 | 容器のキャップ |
| WO2007004038A1 (en) | 2005-07-05 | 2007-01-11 | Pfizer Products Inc. | Aminothiazole derivatives as agonists of the thrombopoietin receptor |
| WO2007008541A2 (en) * | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| CA2617788A1 (en) | 2005-08-04 | 2007-02-15 | Apogee Biotechnology Corporation | Sphingosine kinase inhibitors and methods of their use |
| EP2010554A4 (en) | 2006-05-02 | 2009-06-17 | Univ Washington State | MIG-7 AS SPECIAL ANTIC ACID TARGET |
| WO2008124000A2 (en) * | 2007-04-02 | 2008-10-16 | Ligand Pharmaceuticals Incorporated | Thiazole derivatives as androgen receptor modulator compounds |
| JP4986749B2 (ja) * | 2007-07-09 | 2012-07-25 | 富士フイルム株式会社 | 圧力測定用材料 |
| WO2009014674A1 (en) * | 2007-07-23 | 2009-01-29 | Sirtris Pharmaceuticals, Inc. | Heterocyclylamides as gut microsomal triglyceride transport protein inhibitors |
| CA2724413C (en) | 2008-05-15 | 2016-10-18 | Duke University | Compositions and methods relating to heat shock transcription factor activating compounds and targets thereof |
| US8324385B2 (en) * | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| EP2309273B1 (en) | 2009-09-16 | 2016-05-18 | ZEILLINGER, Robert | Novel tumor marker determination |
| CN103038231B (zh) | 2010-03-17 | 2016-04-20 | 泰纬生命科技股份有限公司 | Hec1活性调节剂及其方法 |
| SG10201506881PA (en) | 2011-11-21 | 2015-10-29 | Taivex Therapeutics Corp | Biomarkers for cancers responsive to modulators of hec1 activity |
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2011
- 2011-03-15 CN CN201180024772.3A patent/CN103038231B/zh active Active
- 2011-03-15 EP EP11756862.6A patent/EP2547676B1/en active Active
- 2011-03-15 US US13/048,709 patent/US8946268B2/en active Active
- 2011-03-15 AU AU2011227398A patent/AU2011227398C1/en active Active
- 2011-03-15 BR BR112012023355A patent/BR112012023355A2/pt not_active Application Discontinuation
- 2011-03-15 SG SG2012064762A patent/SG183853A1/en unknown
- 2011-03-15 CN CN201610159130.9A patent/CN105906617B/zh active Active
- 2011-03-15 JP JP2013500159A patent/JP5825535B2/ja active Active
- 2011-03-15 RU RU2012144022/04A patent/RU2576036C2/ru active
- 2011-03-15 MX MX2012010664A patent/MX2012010664A/es active IP Right Grant
- 2011-03-15 KR KR1020127027026A patent/KR101609856B1/ko active Active
- 2011-03-15 CA CA2793311A patent/CA2793311C/en active Active
- 2011-03-15 MY MYPI2012003984A patent/MY192693A/en unknown
- 2011-03-15 MX MX2015015934A patent/MX346395B/es unknown
- 2011-03-15 NZ NZ602121A patent/NZ602121A/en unknown
- 2011-03-15 ES ES11756862.6T patent/ES2557465T3/es active Active
- 2011-03-15 WO PCT/US2011/028532 patent/WO2011115998A2/en not_active Ceased
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2014
- 2014-08-11 AU AU2014210678A patent/AU2014210678B2/en active Active
- 2014-10-29 US US14/527,087 patent/US9409902B2/en active Active
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2015
- 2015-10-01 JP JP2015196085A patent/JP6294277B2/ja active Active
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