OA11068A - Pharmaceutical aminophosphonic acid derivatives - Google Patents
Pharmaceutical aminophosphonic acid derivatives Download PDFInfo
- Publication number
- OA11068A OA11068A OA9900136A OA9900136A OA11068A OA 11068 A OA11068 A OA 11068A OA 9900136 A OA9900136 A OA 9900136A OA 9900136 A OA9900136 A OA 9900136A OA 11068 A OA11068 A OA 11068A
- Authority
- OA
- OAPI
- Prior art keywords
- hydroxy
- compound
- formula
- diethyl
- methoxy
- Prior art date
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- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title abstract description 5
- 108010033266 Lipoprotein(a) Proteins 0.000 claims abstract description 5
- 102000057248 Lipoprotein(a) Human genes 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- -1 nitro, hydroxy,hydroxymethyl Chemical group 0.000 claims description 18
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002466 imines Chemical class 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 108090001030 Lipoproteins Proteins 0.000 claims description 5
- 102000004895 Lipoproteins Human genes 0.000 claims description 5
- 230000003247 decreasing effect Effects 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 6
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
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- 125000003118 aryl group Chemical group 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
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- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WISXXOGOMDYNSN-UHFFFAOYSA-N 2,6-dimethylpyridin-3-amine Chemical compound CC1=CC=C(N)C(C)=N1 WISXXOGOMDYNSN-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- NVLTWXMZECWWPC-UHFFFAOYSA-N 3-hydroxy-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1OC NVLTWXMZECWWPC-UHFFFAOYSA-N 0.000 description 4
- 241000282567 Macaca fascicularis Species 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
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- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000003304 gavage Methods 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
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000021156 intermittent vascular claudication Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant 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
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 208000030613 peripheral artery disease Diseases 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 230000036470 plasma concentration Effects 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 235000008001 rakum palm Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9626615.0A GB9626615D0 (en) | 1996-12-20 | 1996-12-20 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11068A true OA11068A (en) | 2003-03-10 |
Family
ID=10804837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9900136A OA11068A (en) | 1996-12-20 | 1999-06-18 | Pharmaceutical aminophosphonic acid derivatives |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6303784B1 (no) |
| EP (1) | EP0946572B1 (no) |
| JP (1) | JP2001506667A (no) |
| KR (1) | KR20000069609A (no) |
| CN (1) | CN1105117C (no) |
| AP (1) | AP9901546A0 (no) |
| AR (1) | AR008541A1 (no) |
| AT (1) | ATE255117T1 (no) |
| AU (1) | AU5858898A (no) |
| BG (1) | BG103574A (no) |
| BR (1) | BR9714650A (no) |
| CA (1) | CA2275696A1 (no) |
| CO (1) | CO4930276A1 (no) |
| DE (1) | DE69726449T2 (no) |
| DZ (1) | DZ2377A1 (no) |
| EA (1) | EA199900580A1 (no) |
| GB (1) | GB9626615D0 (no) |
| HU (1) | HUP0002171A3 (no) |
| ID (1) | ID22053A (no) |
| IL (1) | IL130334A0 (no) |
| MA (1) | MA24427A1 (no) |
| NO (1) | NO993001L (no) |
| NZ (1) | NZ335884A (no) |
| OA (1) | OA11068A (no) |
| PE (1) | PE46799A1 (no) |
| PL (1) | PL334189A1 (no) |
| SK (1) | SK81099A3 (no) |
| TR (1) | TR199901423T2 (no) |
| TW (1) | TW434221B (no) |
| WO (1) | WO1998028310A1 (no) |
| ZA (1) | ZA9711431B (no) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001235466B2 (en) | 2000-02-16 | 2004-04-22 | Glaxo Group Limited | Pyrimidine-4-one derivatives as LDL-PLA2 inhibitors |
| JP2003525303A (ja) * | 2000-02-29 | 2003-08-26 | メディキュア インターナショナル インコーポレイテッド | 心臓保護ホスホン酸塩およびマロン酸塩 |
| EP1531157B1 (en) * | 2000-02-29 | 2008-03-19 | Medicure International Inc. | Cardioprotective phosphonates |
| US20030114421A1 (en) * | 2000-09-27 | 2003-06-19 | Phan Hieu Trung | Alpha-substituted beta-aminoethyl phosphonate derivatives |
| CN1489596A (zh) * | 2000-09-27 | 2004-04-14 | �Ʒ� | α-取代的β-氨基乙基膦酸酯类化合物 |
| GB0024808D0 (en) | 2000-10-10 | 2000-11-22 | Smithkline Beecham Plc | Novel compounds |
| GB0025849D0 (en) * | 2000-10-23 | 2000-12-06 | Smithkline Beecham Plc | Novel compounds |
| MXPA04007797A (es) * | 2002-02-11 | 2005-09-08 | Ilex Products Inc | Derivados de fosfonato heteroarilalquilo a-sustituidos. |
| EP1482897A2 (en) * | 2002-02-19 | 2004-12-08 | Ilex Products, Inc. | Aminodiphosphonate apolipoprotein e modulators |
| JP4824968B2 (ja) * | 2005-08-18 | 2011-11-30 | 株式会社クレハ | ホスホン酸誘導体及びその酸付加塩、並びにそれを用いた農園芸用病害防除剤 |
| EP2649053B1 (en) | 2010-12-06 | 2015-11-04 | Glaxo Group Limited | Pyrimidinone compounds for use in the treatment of diseases or conditions mediated by lp-pla2 |
| EP2739627A4 (en) | 2011-07-27 | 2015-01-21 | Glaxo Group Ltd | 2,3-DIHYDROIMIDAZO [1,2-C] PYRIMIDIN-5 (1H) -ONE COMPOUNDS AND USE AS INHIBITORS OF LP-PLA2 |
| US9273054B2 (en) | 2011-07-27 | 2016-03-01 | Glaxo Group Limited | Substituted pyrimido[1,6-a]pyrimidines as Lp-PLA2 inhibitors |
| MY172885A (en) | 2011-09-01 | 2019-12-13 | Glaxo Group Ltd | Novel crystal form |
| RU2015135806A (ru) | 2013-01-25 | 2017-03-03 | Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Соединения |
| KR20150108896A (ko) | 2013-01-25 | 2015-09-30 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Lp-pla2의 억제제로서의 비시클릭 피리미돈 화합물 |
| UY35276A (es) | 2013-01-25 | 2014-08-29 | Glaxosmithkline Ip Dev Ltd | Nuevos compuestos que inhiben la actividad de 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 |
| 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 |
| PE20230092A1 (es) | 2019-11-09 | 2023-01-16 | Shanghai Simr Biotechnology Co Ltd | Derivado triciclico de dihidroimidazopirimidona, metodo de preparacion del mismo, composicion farmaceuticas 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH683996A5 (fr) * | 1992-03-05 | 1994-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant. |
| DE4433244A1 (de) * | 1994-09-19 | 1996-03-28 | Hoechst Ag | Aminomethylphosphon- und Aminomethylphosphinsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen |
| CH690264A5 (fr) | 1995-06-30 | 2000-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et leur utilisation pour la préparation de compositions pharmaceutiques. |
| GB9626536D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
-
1996
- 1996-12-20 GB GBGB9626615.0A patent/GB9626615D0/en active Pending
-
1997
- 1997-12-17 PL PL97334189A patent/PL334189A1/xx unknown
- 1997-12-17 EP EP97954436A patent/EP0946572B1/en not_active Expired - Lifetime
- 1997-12-17 CA CA002275696A patent/CA2275696A1/en not_active Abandoned
- 1997-12-17 JP JP52836498A patent/JP2001506667A/ja active Pending
- 1997-12-17 BR BR9714650-1A patent/BR9714650A/pt not_active Application Discontinuation
- 1997-12-17 ID IDW990550A patent/ID22053A/id unknown
- 1997-12-17 KR KR1019997005605A patent/KR20000069609A/ko not_active Application Discontinuation
- 1997-12-17 WO PCT/EP1997/007161 patent/WO1998028310A1/en not_active Application Discontinuation
- 1997-12-17 US US09/331,385 patent/US6303784B1/en not_active Expired - Fee Related
- 1997-12-17 IL IL13033497A patent/IL130334A0/xx unknown
- 1997-12-17 AP APAP/P/1999/001546A patent/AP9901546A0/en unknown
- 1997-12-17 TR TR1999/01423T patent/TR199901423T2/xx unknown
- 1997-12-17 AU AU58588/98A patent/AU5858898A/en not_active Abandoned
- 1997-12-17 AT AT97954436T patent/ATE255117T1/de not_active IP Right Cessation
- 1997-12-17 SK SK810-99A patent/SK81099A3/sk unknown
- 1997-12-17 EA EA199900580A patent/EA199900580A1/ru unknown
- 1997-12-17 DZ DZ970227A patent/DZ2377A1/xx active
- 1997-12-17 HU HU0002171A patent/HUP0002171A3/hu unknown
- 1997-12-17 DE DE69726449T patent/DE69726449T2/de not_active Expired - Fee Related
- 1997-12-17 NZ NZ335884A patent/NZ335884A/xx unknown
- 1997-12-17 CN CN97180724A patent/CN1105117C/zh not_active Expired - Fee Related
- 1997-12-18 AR ARP970105997A patent/AR008541A1/es unknown
- 1997-12-18 CO CO97073902A patent/CO4930276A1/es unknown
- 1997-12-18 MA MA24903A patent/MA24427A1/fr unknown
- 1997-12-18 PE PE1997001130A patent/PE46799A1/es not_active Application Discontinuation
- 1997-12-19 ZA ZA9711431A patent/ZA9711431B/xx unknown
- 1997-12-20 TW TW086119555A patent/TW434221B/zh active
-
1999
- 1999-06-18 OA OA9900136A patent/OA11068A/en unknown
- 1999-06-18 NO NO993001A patent/NO993001L/no not_active Application Discontinuation
- 1999-07-13 BG BG103574A patent/BG103574A/bg unknown
-
2001
- 2001-09-04 US US09/946,737 patent/US20020082423A1/en not_active Abandoned
Also Published As
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