ES2240070T3 - Uso de sistemas 2-aminotiazoles policiclicos para la fabricacion de medicamentos para el tratamiento de trastornos lipometabolicos, obesidad y diabetes tipo ii. - Google Patents
Uso de sistemas 2-aminotiazoles policiclicos para la fabricacion de medicamentos para el tratamiento de trastornos lipometabolicos, obesidad y diabetes tipo ii.Info
- Publication number
- ES2240070T3 ES2240070T3 ES00910642T ES00910642T ES2240070T3 ES 2240070 T3 ES2240070 T3 ES 2240070T3 ES 00910642 T ES00910642 T ES 00910642T ES 00910642 T ES00910642 T ES 00910642T ES 2240070 T3 ES2240070 T3 ES 2240070T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- conh
- alkynyl
- alkenyl
- 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.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 title claims description 7
- 208000008589 Obesity Diseases 0.000 title claims description 6
- 235000020824 obesity Nutrition 0.000 title claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 4
- 238000011282 treatment Methods 0.000 title description 4
- 208000035475 disorder Diseases 0.000 title description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- -1 alkyl radicals Chemical class 0.000 claims description 24
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000003367 polycyclic group Chemical group 0.000 abstract description 4
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000004480 active ingredient Substances 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- 230000002891 anorexigenic effect Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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- 241001465754 Metazoa Species 0.000 description 4
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- CAJDYMAFIOUARK-UHFFFAOYSA-N 1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)CCC2=C1 CAJDYMAFIOUARK-UHFFFAOYSA-N 0.000 description 3
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- AUHASLVZMRLNKH-UHFFFAOYSA-N 2-chloro-5-pyridin-3-yl-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)C(Cl)CC2=CC=1C1=CC=CN=C1 AUHASLVZMRLNKH-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 238000011785 NMRI mouse Methods 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
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- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- LUJQXGBDWAGQHS-UHFFFAOYSA-N ethenyl acetate;phthalic acid Chemical compound CC(=O)OC=C.OC(=O)C1=CC=CC=C1C(O)=O LUJQXGBDWAGQHS-UHFFFAOYSA-N 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Child & Adolescent Psychology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908538 | 1999-02-26 | ||
| DE19908538A DE19908538A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische 2-Amino-Thiazol Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2240070T3 true ES2240070T3 (es) | 2005-10-16 |
Family
ID=7899082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00910642T Expired - Lifetime ES2240070T3 (es) | 1999-02-26 | 2000-02-05 | Uso de sistemas 2-aminotiazoles policiclicos para la fabricacion de medicamentos para el tratamiento de trastornos lipometabolicos, obesidad y diabetes tipo ii. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6251922B1 (https=) |
| EP (1) | EP1157015B1 (https=) |
| JP (1) | JP4728484B2 (https=) |
| KR (1) | KR20010102390A (https=) |
| CN (1) | CN1148362C (https=) |
| AT (1) | ATE295357T1 (https=) |
| AU (1) | AU763111B2 (https=) |
| BR (1) | BR0008510A (https=) |
| CA (1) | CA2364900A1 (https=) |
| DE (2) | DE19908538A1 (https=) |
| ES (1) | ES2240070T3 (https=) |
| HK (1) | HK1043117B (https=) |
| PT (1) | PT1157015E (https=) |
| WO (1) | WO2000051995A1 (https=) |
| ZA (1) | ZA200106198B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19908537A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| US7732484B2 (en) * | 2000-08-01 | 2010-06-08 | University Of Virginia Patent Foundation | Use of selective adenosine A1 receptor allosteric enhancers to manipulate angiogenesis |
| JP2005529846A (ja) * | 2002-01-16 | 2005-10-06 | ユニバーシティ オブ バージニア パテント ファウンデーション | Ａ１アデノシン受容体の２−アミノチアゾールアロステリックエンハンサ |
| ES2480994T3 (es) | 2008-03-31 | 2014-07-29 | Genentech, Inc. | Compuestos de tipo benzopirano y benzoxepina inhibidores de PI3K y métodos de uso |
| ES2558742T3 (es) | 2009-09-28 | 2016-02-08 | F. Hoffmann-La Roche Ag | Compuestos inhibidores de PI3K de benzoxepina y métodos de uso |
| ES2570569T3 (es) | 2009-09-28 | 2016-05-19 | Hoffmann La Roche | Compuestos de benzoxazepina como inhibidores de la PI3K y métodos de uso |
| JP5728487B2 (ja) * | 2009-10-29 | 2015-06-03 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 三環式ヘテロ環化合物 |
| WO2012126901A1 (en) | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| ES2859478T3 (es) | 2016-09-02 | 2021-10-04 | Bristol Myers Squibb Co | Compuestos heterocíclicos tricíclicos sustituidos |
| WO2019032631A1 (en) | 2017-08-09 | 2019-02-14 | Bristol-Myers Squibb Company | Oxime ether compounds |
| US11046646B2 (en) | 2017-08-09 | 2021-06-29 | Bristol-Myers Squibb Company | Alkylphenyl compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082773A (en) * | 1972-07-03 | 1978-04-04 | E. R. Squibb & Sons, Inc. | Tricyclic tetrahydro naphthaleneols and related compounds |
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| CA1292226C (en) * | 1986-01-16 | 1991-11-19 | Terumi Hachiya | Indenothiazole derivative and process for preparing the same |
| IE68593B1 (en) | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
| TW416953B (en) * | 1996-09-25 | 2001-01-01 | Takeda Chemical Industries Ltd | Tricyclic compounds for eliciting a prostaglandin I2 receptor agonistic effect, their production and use |
| AU3289299A (en) * | 1998-02-19 | 1999-09-06 | Tularik Inc. | Antiviral agents |
| DE19831878C2 (de) * | 1998-07-17 | 2001-05-17 | Aventis Pharma Gmbh | Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE19908537A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
-
1999
- 1999-02-26 DE DE19908538A patent/DE19908538A1/de not_active Withdrawn
-
2000
- 2000-02-05 AU AU32782/00A patent/AU763111B2/en not_active Ceased
- 2000-02-05 BR BR0008510-3A patent/BR0008510A/pt not_active IP Right Cessation
- 2000-02-05 CN CNB008042217A patent/CN1148362C/zh not_active Expired - Fee Related
- 2000-02-05 AT AT00910642T patent/ATE295357T1/de not_active IP Right Cessation
- 2000-02-05 ES ES00910642T patent/ES2240070T3/es not_active Expired - Lifetime
- 2000-02-05 JP JP2000602222A patent/JP4728484B2/ja not_active Expired - Fee Related
- 2000-02-05 PT PT00910642T patent/PT1157015E/pt unknown
- 2000-02-05 DE DE50010285T patent/DE50010285D1/de not_active Expired - Lifetime
- 2000-02-05 CA CA002364900A patent/CA2364900A1/en not_active Abandoned
- 2000-02-05 EP EP00910642A patent/EP1157015B1/de not_active Expired - Lifetime
- 2000-02-05 KR KR1020017010839A patent/KR20010102390A/ko not_active Ceased
- 2000-02-05 WO PCT/EP2000/000924 patent/WO2000051995A1/de not_active Ceased
- 2000-02-05 HK HK02104079.4A patent/HK1043117B/zh not_active IP Right Cessation
- 2000-02-10 US US09/501,208 patent/US6251922B1/en not_active Expired - Lifetime
-
2001
- 2001-07-27 ZA ZA200106198A patent/ZA200106198B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1043117B (zh) | 2004-10-08 |
| DE50010285D1 (de) | 2005-06-16 |
| AU763111B2 (en) | 2003-07-10 |
| CN1148362C (zh) | 2004-05-05 |
| JP4728484B2 (ja) | 2011-07-20 |
| ZA200106198B (en) | 2002-05-03 |
| BR0008510A (pt) | 2002-02-05 |
| DE19908538A1 (de) | 2000-08-31 |
| JP2002538148A (ja) | 2002-11-12 |
| US6251922B1 (en) | 2001-06-26 |
| EP1157015A1 (de) | 2001-11-28 |
| ATE295357T1 (de) | 2005-05-15 |
| PT1157015E (pt) | 2005-08-31 |
| EP1157015B1 (de) | 2005-05-11 |
| KR20010102390A (ko) | 2001-11-15 |
| HK1043117A1 (en) | 2002-09-06 |
| CA2364900A1 (en) | 2000-09-08 |
| WO2000051995A1 (de) | 2000-09-08 |
| AU3278200A (en) | 2000-09-21 |
| CN1344263A (zh) | 2002-04-10 |
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