SK81099A3 - Aminoalkylphosphonic acid drivatives, process for their preparation, pharmaceutical composition containing the same and their use - Google Patents

Aminoalkylphosphonic acid drivatives, process for their preparation, pharmaceutical composition containing the same and their use Download PDF

Info

Publication number: SK81099A3
Authority: SK; Slovakia
Prior art keywords: hydroxy; aminomethylphosphonate; dimethylpyridyl; methoxy; diethyl
Prior art date: 1996-12-20

Application number

SK810-99A

Other languages

English (en)

Slovak (sk)

Inventor

Raymond Azoulay

Craig L Bentzen

Simon Floret

Robert J Ife

Lan Mong Nguyen

Eric Niesor

Hieu Trung Phan

Diep Vinh Van

Original Assignee

Symphar Sa

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.)

1996-12-20

Filing date

1997-12-17

Publication date

1999-11-08

1997-12-17 Application filed by Symphar Sa, Smithkline Beecham Plc filed Critical Symphar Sa

1999-11-08 Publication of SK81099A3 publication Critical patent/SK81099A3/sk

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 7
230000008569 process Effects 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
239000002253 acid Substances 0.000 title description 2
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims abstract description 28
108010033266 Lipoprotein(a) Proteins 0.000 claims abstract description 6
102000057248 Lipoprotein(a) Human genes 0.000 claims abstract 2
-1 nitro, hydroxy, hydroxymethyl Chemical group 0.000 claims description 110
150000001875 compounds Chemical class 0.000 claims description 62
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 31
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 23
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 21
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 19
150000002466 imines Chemical class 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000001118 alkylidene group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
108090001030 Lipoproteins Proteins 0.000 claims description 6
102000004895 Lipoproteins Human genes 0.000 claims description 6
229910052796 boron Inorganic materials 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 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
201000001320 Atherosclerosis Diseases 0.000 claims description 4
241000790917 Dioxys <bee> Species 0.000 claims description 4
208000007536 Thrombosis Diseases 0.000 claims description 3
238000002399 angioplasty Methods 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
208000037803 restenosis Diseases 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino 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
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229910052751 metal Chemical class 0.000 claims description 2
239000002184 metal Chemical class 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 class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000003814 drug Substances 0.000 claims 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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239000000203 mixture Substances 0.000 description 34
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125000003118 aryl group Chemical group 0.000 description 30
238000005481 NMR spectroscopy Methods 0.000 description 20
239000007787 solid Substances 0.000 description 20
239000002904 solvent Substances 0.000 description 20
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239000000460 chlorine Substances 0.000 description 15
238000004440 column chromatography Methods 0.000 description 15
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239000000243 solution Substances 0.000 description 15
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LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
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238000006243 chemical reaction Methods 0.000 description 8
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 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
MGJSDNCLGHCTIL-UHFFFAOYSA-N 4-hydroxy-3-methoxy-5-methylbenzaldehyde Chemical compound COC1=CC(C=O)=CC(C)=C1O MGJSDNCLGHCTIL-UHFFFAOYSA-N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
241000282567 Macaca fascicularis Species 0.000 description 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
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238000001953 recrystallisation Methods 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
NVLTWXMZECWWPC-UHFFFAOYSA-N 3-hydroxy-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1OC NVLTWXMZECWWPC-UHFFFAOYSA-N 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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238000002347 injection Methods 0.000 description 4
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230000036470 plasma concentration Effects 0.000 description 4
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NKODEFQLUSYTTG-UHFFFAOYSA-N 2,6-ditert-butylpyridine-4-carbaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=N1 NKODEFQLUSYTTG-UHFFFAOYSA-N 0.000 description 2
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238000004458 analytical method Methods 0.000 description 2
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238000011161 development Methods 0.000 description 1
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239000012894 fetal calf serum Substances 0.000 description 1
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238000001030 gas--liquid chromatography Methods 0.000 description 1
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239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
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230000002440 hepatic effect Effects 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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230000001900 immune effect Effects 0.000 description 1
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238000011065 in-situ storage Methods 0.000 description 1
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235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 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
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
238000006386 neutralization reaction Methods 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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000000825 pharmaceutical preparation Substances 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
230000035790 physiological processes and functions Effects 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 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
238000002203 pretreatment Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
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239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 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
159000000000 sodium salts Chemical class 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 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
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
230000002537 thrombolytic effect Effects 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
SYUQQUMHOZQROL-UHFFFAOYSA-N trimethylsilyl dihydrogen phosphite Chemical compound C[Si](C)(C)OP(O)O SYUQQUMHOZQROL-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
230000029663 wound healing 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)

SK810-99A 1996-12-20 1997-12-17 Aminoalkylphosphonic acid drivatives, process for their preparation, pharmaceutical composition containing the same and their use SK81099A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9626615.0A GB9626615D0 (en)	1996-12-20	1996-12-20	Novel compounds
PCT/EP1997/007161 WO1998028310A1 (en)	1996-12-20	1997-12-17	Pharmaceutical aminophosphonic acid derivatives

Publications (1)

Publication Number	Publication Date
SK81099A3 true SK81099A3 (en)	1999-11-08

Family

ID=10804837

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK810-99A SK81099A3 (en)	1996-12-20	1997-12-17	Aminoalkylphosphonic acid drivatives, process for their preparation, pharmaceutical composition containing the same and their use

Country Status (31)

Country	Link
US (2)	US6303784B1 (xx)
EP (1)	EP0946572B1 (xx)
JP (1)	JP2001506667A (xx)
KR (1)	KR20000069609A (xx)
CN (1)	CN1105117C (xx)
AP (1)	AP9901546A0 (xx)
AR (1)	AR008541A1 (xx)
AT (1)	ATE255117T1 (xx)
AU (1)	AU5858898A (xx)
BG (1)	BG103574A (xx)
BR (1)	BR9714650A (xx)
CA (1)	CA2275696A1 (xx)
CO (1)	CO4930276A1 (xx)
DE (1)	DE69726449T2 (xx)
DZ (1)	DZ2377A1 (xx)
EA (1)	EA199900580A1 (xx)
GB (1)	GB9626615D0 (xx)
HU (1)	HUP0002171A3 (xx)
ID (1)	ID22053A (xx)
IL (1)	IL130334A0 (xx)
MA (1)	MA24427A1 (xx)
NO (1)	NO993001L (xx)
NZ (1)	NZ335884A (xx)
OA (1)	OA11068A (xx)
PE (1)	PE46799A1 (xx)
PL (1)	PL334189A1 (xx)
SK (1)	SK81099A3 (xx)
TR (1)	TR199901423T2 (xx)
TW (1)	TW434221B (xx)
WO (1)	WO1998028310A1 (xx)
ZA (1)	ZA9711431B (xx)

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ATE437862T1 (de)	2000-02-16	2009-08-15	Smithkline Beecham Plc	Pyrimidin-5-onderivate als ldl-pla2 inhibitoren
US7442689B2 (en)	2000-02-29	2008-10-28	Medicure International Inc.	Cardioprotective phosphonates and malonates
EP1531157B1 (en) *	2000-02-29	2008-03-19	Medicure International Inc.	Cardioprotective phosphonates
DE60133323T2 (de) *	2000-02-29	2009-03-05	Medicure International Inc.	Cardioprotektive Phosphonate
US6897228B2 (en)	2000-07-07	2005-05-24	Medicure International Inc.	Pyridoxine and pyridoxal analogues: new uses
EP1320536A1 (en)	2000-09-27	2003-06-25	Ilex Oncology Research S.A.	$g(a)-SUBSTITUTED $g(b)-AMINOETHYL PHOSPHONATES
US20030114421A1 (en) *	2000-09-27	2003-06-19	Phan Hieu Trung	Alpha-substituted beta-aminoethyl phosphonate derivatives
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
AU2003219701A1 (en) *	2002-02-11	2003-09-04	Ilex Products, Inc.	Alpha-substituted heteroarylalkyl phosphonate derivatives
EP1482897A2 (en) *	2002-02-19	2004-12-08	Ilex Products, Inc.	Aminodiphosphonate apolipoprotein e modulators
US7459468B2 (en)	2004-10-28	2008-12-02	Medicure International, Inc.	Aryl sulfonic pyridoxines as antiplatelet agents
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
UY33766A (es)	2010-12-06	2012-06-29	Glaxo Group Ltd	COMPUESTOS CON ESTRUCTURA DE PIRIMIDINONA PARA USO EN EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR Lp-PLA2
WO2013013503A1 (en)	2011-07-27	2013-01-31	Glaxo Group Limited	2,3-dihydroimidazo[1,2-c] pyrimidin-5(1h)-one compounds use as lp-pla2 inhibitors
TW201321382A (zh)	2011-07-27	2013-06-01	Glaxo Group Ltd	化合物
MY172885A (en)	2011-09-01	2019-12-13	Glaxo Group Ltd	Novel crystal form
PE20151251A1 (es)	2013-01-25	2015-09-10	Glaxosmithkline Ip Dev Ltd	Derivados [5,6] biciclicos de imidazo pirimidona con actividad sobre enzimas lp-pla2
AU2014210259B2 (en)	2013-01-25	2016-11-03	Glaxosmithkline Intellectual Property Development Limited	Compounds
WO2014114249A1 (en)	2013-01-25	2014-07-31	Glaxosmithkline Intellectual Property Development Limited	Bicyclic pyrimidone compounds as inhibitors of 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
EP4056571A4 (en)	2019-11-09	2024-01-24	Shanghai Simr Biotechnology Co., Ltd.	TRICYCLIC DIHYDROIMIDAZOPYRIMIDONE DERIVATIVE, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL COMPOSITION AND USE THEREOF
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)

* Cited by examiner, † Cited by third party
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 AU AU58588/98A patent/AU5858898A/en not_active Abandoned
- 1997-12-17 ID IDW990550A patent/ID22053A/id unknown
- 1997-12-17 KR KR1019997005605A patent/KR20000069609A/ko not_active Ceased
- 1997-12-17 EA EA199900580A patent/EA199900580A1/ru unknown
- 1997-12-17 SK SK810-99A patent/SK81099A3/sk unknown
- 1997-12-17 WO PCT/EP1997/007161 patent/WO1998028310A1/en not_active Ceased
- 1997-12-17 BR BR9714650-1A patent/BR9714650A/pt not_active Application Discontinuation
- 1997-12-17 AT AT97954436T patent/ATE255117T1/de not_active IP Right Cessation
- 1997-12-17 NZ NZ335884A patent/NZ335884A/xx unknown
- 1997-12-17 US US09/331,385 patent/US6303784B1/en not_active Expired - Fee Related
- 1997-12-17 PL PL97334189A patent/PL334189A1/xx unknown
- 1997-12-17 TR TR1999/01423T patent/TR199901423T2/xx unknown
- 1997-12-17 IL IL13033497A patent/IL130334A0/xx unknown
- 1997-12-17 HU HU0002171A patent/HUP0002171A3/hu unknown
- 1997-12-17 AP APAP/P/1999/001546A patent/AP9901546A0/en unknown
- 1997-12-17 DZ DZ970227A patent/DZ2377A1/xx active
- 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 CN CN97180724A patent/CN1105117C/zh not_active Expired - Fee Related
- 1997-12-17 DE DE69726449T patent/DE69726449T2/de not_active Expired - Fee Related
- 1997-12-18 CO CO97073902A patent/CO4930276A1/es unknown
- 1997-12-18 PE PE1997001130A patent/PE46799A1/es not_active Application Discontinuation
- 1997-12-18 MA MA24903A patent/MA24427A1/fr unknown
- 1997-12-18 AR ARP970105997A patent/AR008541A1/es unknown
- 1997-12-19 ZA ZA9711431A patent/ZA9711431B/xx unknown
- 1997-12-20 TW TW086119555A patent/TW434221B/zh active
1999
- 1999-06-18 NO NO993001A patent/NO993001L/no not_active Application Discontinuation
- 1999-06-18 OA OA9900136A patent/OA11068A/en unknown
- 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

Publication number	Publication date
EP0946572B1 (en)	2003-11-26
AP9901546A0 (en)	1999-06-30
ZA9711431B (en)	1999-06-21
CN1240451A (zh)	2000-01-05
NZ335884A (en)	2000-11-24
AR008541A1 (es)	2000-01-19
WO1998028310A1 (en)	1998-07-02
NO993001D0 (no)	1999-06-18
BR9714650A (pt)	2000-10-03
HUP0002171A3 (en)	2002-12-28
US20020082423A1 (en)	2002-06-27
PE46799A1 (es)	1999-06-24
CA2275696A1 (en)	1998-07-02
CO4930276A1 (es)	2000-06-27
ATE255117T1 (de)	2003-12-15
TR199901423T2 (xx)	1999-10-21
DE69726449D1 (en)	2004-01-08
DE69726449T2 (de)	2004-08-26
KR20000069609A (ko)	2000-11-25
NO993001L (no)	1999-06-18
ID22053A (id)	1999-08-26
EA199900580A1 (ru)	1999-12-29
BG103574A (bg)	2000-11-30
HUP0002171A2 (hu)	2001-05-28
OA11068A (en)	2003-03-10
CN1105117C (zh)	2003-04-09
PL334189A1 (en)	2000-02-14
DZ2377A1 (fr)	2002-12-28
JP2001506667A (ja)	2001-05-22
TW434221B (en)	2001-05-16
IL130334A0 (en)	2000-06-01
AU5858898A (en)	1998-07-17
GB9626615D0 (en)	1997-02-05
EP0946572A1 (en)	1999-10-06
US6303784B1 (en)	2001-10-16
MA24427A1 (fr)	1998-07-01

Publication	Publication Date	Title
US6303784B1 (en)	2001-10-16	Pharmaceutical aminophosphonic acid derivatives
US6660724B1 (en)	2003-12-09	Compounds and pharmaceutical compositions containing them
MXPA98000189A (en)	1998-04-01	Compounds and pharmaceutical compositions that contains them
WO1998028311A1 (en)	1998-07-02	Pharmaceutical aminophosphonic acid derivatives
WO1998028312A1 (en)	1998-07-02	Pharmaceutical aminophosphonic acid derivatives
AU2001294792B2 (en)	2006-12-14	Alpha-substituted beta-aminoethyl phosphonates
AU2001294792A1 (en)	2002-06-20	Alpha-substituted beta-aminoethyl phosphonates
CZ219699A3 (cs)	2000-02-16	Farmaceutické deriváty kyseliny aminofosfonové
US20030114421A1 (en)	2003-06-19	Alpha-substituted beta-aminoethyl phosphonate derivatives
US6872711B2 (en)	2005-03-29	β-substituted β-aminoethyl phosphonate derivatives
JP2005529071A (ja)	2005-09-29	α−置換ヘテロアリールアルキルホスホン酸エステル誘導体
JP2005517711A (ja)	2005-06-16	α−置換アリールアルキルホスホン酸エステル誘導体