ZA200403186B - Heterocyclic derivatives of glycinamide and their medical use. - Google Patents

Heterocyclic derivatives of glycinamide and their medical use. Download PDF

Info

Publication number: ZA200403186B
Authority: ZA; South Africa
Prior art keywords: ethyl; oxo; methyl; quinolin; difluorophenyl
Prior art date: 2001-11-10

Application number

ZA200403186A

Other languages

English (en)

Inventor

Richard Leonard Elliot

Deirdre Mary Bernadette Hickey

Robert John Ife

Colin Andrew Leach

John Liddle

Ivan Leo Pinto

Steven James Stanway

Stephen Allan Smith

Original Assignee

Smithkline Beecham Plc

Priority date (The priority date 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 date listed.)

2001-11-10

Filing date

2004-04-28

Publication date

2005-01-14

2004-04-28 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2005-01-14 Publication of ZA200403186B publication Critical patent/ZA200403186B/en

Links

125000000623 heterocyclic group Chemical group 0.000 title claims description 24
150000001875 compounds Chemical class 0.000 claims description 93
125000000217 alkyl group Chemical group 0.000 claims description 77
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 47
125000003545 alkoxy group Chemical group 0.000 claims description 46
-1 anlCe1-gyalkoxy Chemical group 0.000 claims description 44
125000001424 substituent group Chemical group 0.000 claims description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002367 halogens Chemical class 0.000 claims description 36
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 33
125000003118 aryl group Chemical group 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
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150000003839 salts Chemical class 0.000 claims description 14
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 13
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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230000000694 effects Effects 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
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YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 claims description 4
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150000001408 amides Chemical class 0.000 claims description 4
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125000005843 halogen group Chemical group 0.000 claims description 4
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
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UQRFSLFJOMQMTP-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[2-[2-(2,3-difluorophenyl)ethyl]-4-oxo-7-(trifluoromethyl)quinazolin-1-yl]-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CCC1=NC(=O)C2=CC=C(C(F)(F)F)C=C2N1CC(=O)N(CCN(CC)CC)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UQRFSLFJOMQMTP-UHFFFAOYSA-N 0.000 claims description 2
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UGIWIBLARUSYCI-UHFFFAOYSA-N 2-[2-[2-(2,3-difluorophenyl)ethyl]-4-oxo-7-(2-piperidin-1-ylethoxy)quinolin-1-yl]-n-methyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CCC1=CC(=O)C2=CC=C(OCCN3CCCCC3)C=C2N1CC(=O)N(C)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UGIWIBLARUSYCI-UHFFFAOYSA-N 0.000 claims 1
DSMFOWBYBVPINR-UHFFFAOYSA-N 2-[2-[2-(2,3-difluorophenyl)ethyl]-4-oxo-7-(2-pyrrolidin-1-ylethyl)quinolin-1-yl]-n-methyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CCC1=CC(=O)C2=CC=C(CCN3CCCC3)C=C2N1CC(=O)N(C)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 DSMFOWBYBVPINR-UHFFFAOYSA-N 0.000 claims 1
YPAALVSCLPQHDI-UHFFFAOYSA-N 2-[2-[2-(2,3-difluorophenyl)ethyl]-7-[(1-methylpyrrolidin-2-yl)methoxy]-4-oxoquinolin-1-yl]-n-methyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CCC1=CC(=O)C2=CC=C(OCC3N(CCC3)C)C=C2N1CC(=O)N(C)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 YPAALVSCLPQHDI-UHFFFAOYSA-N 0.000 claims 1
NZWBSAGYEROVMA-UHFFFAOYSA-N 2-[2-[2-(2,3-difluorophenyl)ethyl]-7-[2-(dimethylamino)ethyl]-4-oxoquinolin-1-yl]-n-methyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C(CCN(C)C)=CC=C(C(C=C2CCC=3C(=C(F)C=CC=3)F)=O)C=1N2CC(=O)N(C)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 NZWBSAGYEROVMA-UHFFFAOYSA-N 0.000 claims 1
CVWBGWXGUSQXNH-UHFFFAOYSA-N 2-[7-(diethylaminomethyl)-2-[2-(2,3-difluorophenyl)ethyl]-4-oxoquinolin-1-yl]-n-propan-2-yl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C(CN(CC)CC)=CC=C(C(C=C2CCC=3C(=C(F)C=CC=3)F)=O)C=1N2CC(=O)N(C(C)C)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 CVWBGWXGUSQXNH-UHFFFAOYSA-N 0.000 claims 1
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PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000028550 monocyte chemotaxis Effects 0.000 description 1
210000004980 monocyte derived macrophage Anatomy 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
AODSSUGFSXJMBT-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[2-[2-(2,3-difluorophenyl)ethyl]-7-methyl-4-oxo-1,8-naphthyridin-1-yl]-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CCC1=CC(=O)C2=CC=C(C)N=C2N1CC(=O)N(CCN(CC)CC)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 AODSSUGFSXJMBT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MTAATKPKQMGFET-UHFFFAOYSA-N n-propan-2-yl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C1=CC(CN(C(C)C)C(C)=O)=CC=C1C1=CC=C(C(F)(F)F)C=C1 MTAATKPKQMGFET-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
229920001432 poly(L-lactide) Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000207 pro-atherogenic effect Effects 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
150000008318 pyrimidones Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
229960000672 rosuvastatin Drugs 0.000 description 1
BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 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
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Hydrogenated Pyridines (AREA)
Quinoline Compounds (AREA)

ZA200403186A 2001-11-10 2004-04-28 Heterocyclic derivatives of glycinamide and their medical use. ZA200403186B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0127141.0A GB0127141D0 (en)	2001-11-10	2001-11-10	Novel compounds

Publications (1)

Publication Number	Publication Date
ZA200403186B true ZA200403186B (en)	2005-01-14

Family

ID=9925627

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200403186A ZA200403186B (en)	2001-11-10	2004-04-28	Heterocyclic derivatives of glycinamide and their medical use.

Country Status (19)

Country	Link
US (1)	US20050043335A1 (zh)
EP (1)	EP1442020A1 (zh)
JP (1)	JP2005511622A (zh)
KR (1)	KR20050044366A (zh)
CN (1)	CN1289483C (zh)
AU (1)	AU2002351921B2 (zh)
BR (1)	BR0213994A (zh)
CA (1)	CA2468497A1 (zh)
CO (1)	CO5580825A2 (zh)
GB (1)	GB0127141D0 (zh)
HU (1)	HUP0402244A2 (zh)
IL (1)	IL161854A0 (zh)
MX (1)	MXPA04004372A (zh)
NO (1)	NO20042406L (zh)
NZ (1)	NZ532520A (zh)
PL (1)	PL369521A1 (zh)
RU (1)	RU2004117603A (zh)
WO (1)	WO2003042179A1 (zh)
ZA (1)	ZA200403186B (zh)

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EP1887000A4 (en) *	2005-05-27	2011-09-07	Shionogi & Co	ARYLACETATE DERIVATIVES WITH ISOXAZO EASY
US7705005B2 (en) *	2006-10-13	2010-04-27	Glaxo Group Limited	Bicyclic heteroaromatic compounds
AU2008251467B2 (en)	2007-05-11	2014-07-31	The Trustees Of The University Of Pennsylvania	Methods of treatment of skin ulcers
US8962633B2 (en)	2007-05-11	2015-02-24	Thomas Jefferson University	Methods of treatment and prevention of metabolic bone diseases and disorders
BRPI0721697A2 (pt)	2007-05-11	2014-08-05	Univ Jefferson	" métodos para tratar e/ou prevenir uma doença ou distúrbio neurodegenerativo em um indivíduo, para tratar e/ou prevenir um indivíduo com ou em risco de demência vascular, para tratar e/ou prevenir uma doença ou distúrbio associado com uma barreira hematoencefálica anormal em um indivíduo, para diminuir o acúmulo beta amilóide no cérebro de um indivíduo, para tratar e/ou prevenir mal de alzheimer em um indivíduo e para prevenir ou reduzir o risco de desenvolver mal de alzhheimer, e, uso de um agente que inibe a expressão e/ou atividade da proteína lp-pla2."
WO2012076435A1 (en)	2010-12-06	2012-06-14	Glaxo Group Limited	Pyrimidinone compounds for use in the treatment of diseases or conditions mediated by lp - pla2
WO2012080497A2 (en)	2010-12-17	2012-06-21	Glaxo Group Limited	Methods of treatment and prevention of eye diseases
WO2013000267A1 (zh)	2011-06-27	2013-01-03	中国科学院上海药物研究所	唑类杂环化合物、其制备方法、药物组合物和用途
BR112014001665A2 (pt)	2011-07-27	2017-02-14	Glaxo Group Ltd	compostos de 2,3-di-hidroimidazo[1,2-c]pirimidin-5(1h)-ona utilizados como inibidores de lp-plaz
TW201321382A (zh)	2011-07-27	2013-06-01	Glaxo Group Ltd	化合物
EP2760840B1 (en)	2011-09-30	2015-08-12	Bristol-Myers Squibb Company	Quinolinone carboxamide inhibitors of endothelial lipase
UY35276A (es)	2013-01-25	2014-08-29	Glaxosmithkline Ip Dev Ltd	Nuevos compuestos que inhiben la actividad de Lp-PLA2
BR112015017397A2 (pt)	2013-01-25	2017-07-11	Glaxosmithkline Ip Dev Ltd	compostos pirimidona bicíclica como inibidores de lp-pla2
KR20150111356A (ko)	2013-01-25	2015-10-05	글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드	화합물
WO2016012917A1 (en)	2014-07-22	2016-01-28	Glaxosmithkline Intellectual Property Development Limited	1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2
WO2016012916A1 (en)	2014-07-22	2016-01-28	Glaxosmithkline Intellectual Property Development Limited	1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2
MX2022005615A (es)	2019-11-09	2022-07-27	Shanghai Simr Biotechnology Co Ltd	Derivado triciclico de dihidroimidazopirimidona, metodo de preparacion del mismo, composicion farmaceutica y uso del mismo.
CN115304620A (zh)	2021-05-07	2022-11-08	上海赛默罗生物科技有限公司	嘧啶酮衍生物、其制备方法、药物组合物和用途

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Publication number	Priority date	Publication date	Assignee	Title
CZ304450B6 (cs) *	2000-02-16	2014-05-14	Smithkline Beecham P. L. C.	Pyrimidinový derivát

2001
- 2001-11-10 GB GBGB0127141.0A patent/GB0127141D0/en not_active Ceased
2002
- 2002-11-08 BR BR0213994-4A patent/BR0213994A/pt not_active IP Right Cessation
- 2002-11-08 US US10/494,509 patent/US20050043335A1/en not_active Abandoned
- 2002-11-08 CN CNB028259688A patent/CN1289483C/zh not_active Expired - Fee Related
- 2002-11-08 RU RU2004117603/04A patent/RU2004117603A/ru not_active Application Discontinuation
- 2002-11-08 HU HU0402244A patent/HUP0402244A2/hu unknown
- 2002-11-08 PL PL02369521A patent/PL369521A1/xx not_active Application Discontinuation
- 2002-11-08 EP EP02787607A patent/EP1442020A1/en not_active Withdrawn
- 2002-11-08 JP JP2003544015A patent/JP2005511622A/ja active Pending
- 2002-11-08 KR KR1020047006964A patent/KR20050044366A/ko not_active Application Discontinuation
- 2002-11-08 AU AU2002351921A patent/AU2002351921B2/en not_active Ceased
- 2002-11-08 WO PCT/EP2002/012505 patent/WO2003042179A1/en not_active Application Discontinuation
- 2002-11-08 NZ NZ532520A patent/NZ532520A/en unknown
- 2002-11-08 IL IL16185402A patent/IL161854A0/xx unknown
- 2002-11-08 MX MXPA04004372A patent/MXPA04004372A/es unknown
- 2002-11-08 CA CA002468497A patent/CA2468497A1/en not_active Abandoned
2004
- 2004-04-28 ZA ZA200403186A patent/ZA200403186B/en unknown
- 2004-05-07 CO CO04042442A patent/CO5580825A2/es not_active Application Discontinuation
- 2004-06-09 NO NO20042406A patent/NO20042406L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1608053A (zh)	2005-04-20
AU2002351921B2 (en)	2007-01-25
PL369521A1 (en)	2005-04-18
NO20042406L (no)	2004-06-09
CN1289483C (zh)	2006-12-13
CO5580825A2 (es)	2005-11-30
NZ532520A (en)	2006-12-22
BR0213994A (pt)	2004-08-31
HUP0402244A2 (hu)	2005-02-28
WO2003042179A1 (en)	2003-05-22
GB0127141D0 (en)	2002-01-02
RU2004117603A (ru)	2005-04-20
IL161854A0 (en)	2005-11-20
CA2468497A1 (en)	2003-05-22
JP2005511622A (ja)	2005-04-28
EP1442020A1 (en)	2004-08-04
US20050043335A1 (en)	2005-02-24
MXPA04004372A (es)	2004-08-11
KR20050044366A (ko)	2005-05-12

Publication	Publication Date	Title
JP4212354B2 (ja)	2009-01-21	アテローム性動脈硬化の治療のためのピリジノン誘導体
ZA200403186B (en)	2005-01-14	Heterocyclic derivatives of glycinamide and their medical use.
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