OA12782A - Oxo-azabicyclic compounds. - Google Patents

Oxo-azabicyclic compounds. Download PDF

Info

Publication number: OA12782A
Authority: OA; OAPI
Prior art keywords: formula; compound; oxo; methoxy; group
Prior art date: 2002-03-08

Application number

OA1200400234A

Other languages

English (en)

Inventor

Bernard Gaudilliere

Henry Jacobelli

Catherine Kostlan

Jack Li

Wen-Song Yue

Original Assignee

Warner Lambert Co

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.)

2002-03-08

Filing date

2003-03-06

Publication date

2006-07-10

2003-03-06 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2006-07-10 Publication of OA12782A publication Critical patent/OA12782A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 282
125000000217 alkyl group Chemical group 0.000 claims abstract description 70
239000002253 acid Substances 0.000 claims abstract description 23
229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 18
150000001204 N-oxides Chemical class 0.000 claims abstract description 16
239000011159 matrix material Substances 0.000 claims abstract description 14
229910052799 carbon Inorganic materials 0.000 claims abstract description 11
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 8
239000005711 Benzoic acid Substances 0.000 claims description 52
238000000034 method Methods 0.000 claims description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
-1 4-methoxy-benzylamide - 3-(4-methoxy-benzyl)-1,2,2-trimethyl-4-oxo-1,2,3,4-tetrahydro-quinazoline-6-carboxylic acid 4-methoxy-benzylamide Chemical compound 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
201000008482 osteoarthritis Diseases 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
239000005864 Sulphur Substances 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 7
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 7
108010006035 Metalloproteases Proteins 0.000 claims description 6
102000005741 Metalloproteases Human genes 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
238000000746 purification Methods 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
206010019280 Heart failures Diseases 0.000 claims description 5
208000001132 Osteoporosis Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
206010064930 age-related macular degeneration Diseases 0.000 claims description 5
206010003246 arthritis Diseases 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
208000002780 macular degeneration Diseases 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
208000028169 periodontal disease Diseases 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
UQAHBOKPZNLKRF-UHFFFAOYSA-N (2-methoxypyridin-4-yl)methanamine Chemical compound COC1=CC(CN)=CC=N1 UQAHBOKPZNLKRF-UHFFFAOYSA-N 0.000 claims description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
150000004678 hydrides Chemical class 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
ZXNYEDZBKKWZOL-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methyl]-n-[(4-methoxyphenyl)methyl]-4-oxoquinazoline-6-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C(N=CN(CC=2C=C(F)C(F)=CC=2)C2=O)C2=C1 ZXNYEDZBKKWZOL-UHFFFAOYSA-N 0.000 claims description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 2
OJHFOZDTLSSJAG-UHFFFAOYSA-N 3-[(3-fluorophenyl)methyl]-n-[(3-methoxyphenyl)methyl]-4-oxopyrido[3,4-d]pyrimidine-6-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2N=CC3=C(C(N(CC=4C=C(F)C=CC=4)C=N3)=O)C=2)=C1 OJHFOZDTLSSJAG-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
229910052763 palladium Inorganic materials 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 10
229910052717 sulfur Inorganic materials 0.000 abstract description 7
230000003287 optical effect Effects 0.000 abstract description 3
125000003342 alkenyl group Chemical group 0.000 abstract description 2
125000000304 alkynyl group Chemical group 0.000 abstract 1
229940126601 medicinal product Drugs 0.000 abstract 1
239000000243 solution Substances 0.000 description 56
229960004365 benzoic acid Drugs 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 26
230000003197 catalytic effect Effects 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 21
239000012044 organic layer Substances 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 18
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
229940050390 benzoate Drugs 0.000 description 13
238000003818 flash chromatography Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
229960001866 silicon dioxide Drugs 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 12
239000012267 brine Substances 0.000 description 12
125000000753 cycloalkyl group Chemical group 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
125000001072 heteroaryl group Chemical group 0.000 description 11
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000000758 substrate Substances 0.000 description 10
NGKSKVYWPINGLI-UHFFFAOYSA-N prop-2-ynylbenzene Chemical group C#CCC1=CC=CC=C1 NGKSKVYWPINGLI-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
125000000592 heterocycloalkyl group Chemical group 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000003039 volatile agent Substances 0.000 description 8
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 7
125000003282 alkyl amino group Chemical group 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000012360 testing method Methods 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 5
GRRIMVWABNHKBX-UHFFFAOYSA-N (3-methoxyphenyl)methanamine Chemical compound COC1=CC=CC(CN)=C1 GRRIMVWABNHKBX-UHFFFAOYSA-N 0.000 description 4
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
230000005587 bubbling Effects 0.000 description 4
210000000845 cartilage Anatomy 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
238000010791 quenching Methods 0.000 description 4
230000000171 quenching effect Effects 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 3
ICGYHHIJQXSEQH-UHFFFAOYSA-N 4-[[4-oxo-6-(3-phenylprop-1-ynyl)quinazolin-3-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(=O)C2=CC(C#CCC=3C=CC=CC=3)=CC=C2N=C1 ICGYHHIJQXSEQH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 3
229940124761 MMP inhibitor Drugs 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229910002666 PdCl2 Inorganic materials 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
230000006378 damage Effects 0.000 description 3
210000002744 extracellular matrix Anatomy 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
230000007170 pathology Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 2
SMPOZSZTZOCPHG-UHFFFAOYSA-N 3-[(3-fluorophenyl)methyl]-4-oxopyrido[3,4-d]pyrimidine-6-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC(C2=O)=C1N=CN2CC1=CC=CC(F)=C1 SMPOZSZTZOCPHG-UHFFFAOYSA-N 0.000 description 2
AKFOYYXBYKQZDK-UHFFFAOYSA-N 6-(3-phenylprop-1-ynyl)-3-(pyridin-4-ylmethyl)quinazolin-4-one Chemical compound C1=NC2=CC=C(C#CCC=3C=CC=CC=3)C=C2C(=O)N1CC1=CC=NC=C1 AKFOYYXBYKQZDK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
108010000684 Matrix Metalloproteinases Proteins 0.000 description 2
102000002274 Matrix Metalloproteinases Human genes 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FPQVGDGSRVMNMR-JCTPKUEWSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCOC(=O)C(\C#N)=N/OC(N(C)C)=[N+](C)C FPQVGDGSRVMNMR-JCTPKUEWSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000012190 activator Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
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125000005605 benzo group Chemical group 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
230000007850 degeneration Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
230000017854 proteolysis Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
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PSFGVWUWJYYRGT-UHFFFAOYSA-N n-[4-[[4-oxo-6-(3-phenylprop-1-ynyl)quinazolin-3-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1C(=O)C2=CC(C#CCC=3C=CC=CC=3)=CC=C2N=C1 PSFGVWUWJYYRGT-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000011017 operating method Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229940116315 oxalic acid Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000080 stannane Inorganic materials 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
210000002435 tendon Anatomy 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 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
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
210000003934 vacuole Anatomy 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
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Vascular Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

OA1200400234A 2002-03-08 2003-03-06 Oxo-azabicyclic compounds. OA12782A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/EP2002/003240 WO2003076416A1 (en)	2002-03-08	2002-03-08	Oxo azabicyclic compounds

Publications (1)

Publication Number	Publication Date
OA12782A true OA12782A (en)	2006-07-10

Family

ID=27798761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200400234A OA12782A (en)	2002-03-08	2003-03-06	Oxo-azabicyclic compounds.

Country Status (25)

Country	Link
EP (1)	EP1492775A2 (pl)
JP (1)	JP2005526070A (pl)
KR (1)	KR20040095270A (pl)
CN (1)	CN1738806A (pl)
AP (1)	AP2004003125A0 (pl)
AR (1)	AR039562A1 (pl)
AU (2)	AU2002249275A1 (pl)
BR (1)	BR0308280A (pl)
CA (1)	CA2478706A1 (pl)
CO (1)	CO5601020A2 (pl)
EA (1)	EA200401053A1 (pl)
EC (1)	ECSP045278A (pl)
IL (1)	IL163818A0 (pl)
IS (1)	IS7414A (pl)
MA (1)	MA27183A1 (pl)
MX (1)	MXPA04008681A (pl)
NO (1)	NO20044041L (pl)
OA (1)	OA12782A (pl)
PA (1)	PA8568501A1 (pl)
PE (1)	PE20031018A1 (pl)
PL (1)	PL372622A1 (pl)
SV (1)	SV2003001495A (pl)
TN (1)	TNSN04169A1 (pl)
UY (1)	UY27700A1 (pl)
WO (2)	WO2003076416A1 (pl)

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PA8539501A1 (es)	2001-02-14	2002-09-30	Warner Lambert Co	Compuestos triazolo como inhibidores de mmp
US6962922B2 (en)	2001-10-12	2005-11-08	Warner-Lambert Company Llc	Alkynylated quinazoline compounds
US6894057B2 (en)	2002-03-08	2005-05-17	Warner-Lambert Company	Oxo-azabicyclic compounds
MXPA05001786A (es)	2002-08-13	2005-04-25	Warner Lambert Co	Derivados de azaisoquinolina como inhibidores de la metaloproteinasa de matriz.
AU2003249540A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Fused bicyclic metalloproteinase inhibitors
WO2004014909A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors
WO2004014892A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Monocyclic derivatives as matrix metalloproteinase inhibitors
JP2006500351A (ja)	2002-08-13	2006-01-05	ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー	マトリックスメタロプロテアーゼ−１３阻害剤としてのピリミジン−２，４−ジオン誘導体
WO2004014923A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Pyrimidinone fused bicyclic metalloproteinase inhibitors
AU2003250466A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	3-isoquinolinone derivatives as matrix metalloproteinase inhiitors
WO2004014384A2 (en) *	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors
AU2003253150A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Chromone derivatives as matrix metalloproteinase inhibitors
PA8578101A1 (es)	2002-08-13	2004-05-07	Warner Lambert Co	Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz
WO2005016926A1 (en) *	2003-08-19	2005-02-24	Warner-Lambert Company Llc	Pyrido [3,4-d] pyrimidine derivatives as matrix metalloproteinase-13 inhibitors
DE10360835A1 (de) *	2003-12-23	2005-07-21	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Bicyclische Imidazolverbindungen, deren Herstellung und deren Verwendung als Arzneimittel
CN1976907A (zh) *	2004-04-30	2007-06-06	武田药品工业株式会社	杂环酰胺化合物及其作为mmp－13抑制剂的用途
CA2568756A1 (en) *	2004-06-15	2005-12-29	Astrazeneca Ab	Substituted quinazolones as anti-cancer agents
CN101522676A (zh)	2006-10-05	2009-09-02	Cv医药有限公司	用作硬脂酰-CoA脱氢酶抑制剂的双环含氮杂环化合物
WO2012052451A1 (en)	2010-10-18	2012-04-26	Merz Pharma Gmbh & Co. Kgaa	Metabotropic glutamate receptor modulators
CN103524431B (zh) *	2013-09-24	2016-01-13	西安交通大学	3-苄基-4-喹唑啉酮类化合物及其合成方法和应用
JO3512B1 (ar)	2014-03-26	2020-07-05	Astex Therapeutics Ltd	مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز
KR102703498B1 (ko)	2015-09-23	2024-09-04	얀센 파마슈티카 엔브이	신규 화합물
CN108137546B (zh)	2015-09-23	2021-07-27	詹森药业有限公司	双杂芳基取代的1,4-苯并二氮杂卓化合物及其用于治疗癌症的用途
FR3046793B1 (fr) *	2016-01-14	2018-01-05	Les Laboratoires Servier	Nouveaux derives de phosphinanes et azaphosphinanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

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AU5380398A (en) *	1996-12-17	1998-07-15	E.I. Du Pont De Nemours And Company	Fungicidal quinazolinones
PA8539401A1 (es) *	2001-02-14	2002-10-28	Warner Lambert Co	Quinazolinas como inhibidores de mmp-13
PA8539301A1 (es) *	2001-02-14	2002-09-30	Warner Lambert Co	Inhibidores de la metaloproteinasa de la matriz

2002
- 2002-03-08 AU AU2002249275A patent/AU2002249275A1/en not_active Abandoned
- 2002-03-08 WO PCT/EP2002/003240 patent/WO2003076416A1/en not_active Ceased
2003
- 2003-03-04 SV SV2003001495A patent/SV2003001495A/es not_active Application Discontinuation
- 2003-03-06 EP EP03708181A patent/EP1492775A2/en not_active Withdrawn
- 2003-03-06 PE PE2003000218A patent/PE20031018A1/es not_active Application Discontinuation
- 2003-03-06 CA CA002478706A patent/CA2478706A1/en not_active Abandoned
- 2003-03-06 AP APAP/P/2004/003125A patent/AP2004003125A0/en unknown
- 2003-03-06 AR ARP030100749A patent/AR039562A1/es not_active Application Discontinuation
- 2003-03-06 JP JP2003574636A patent/JP2005526070A/ja not_active Withdrawn
- 2003-03-06 WO PCT/EP2003/002277 patent/WO2003076417A2/en not_active Ceased
- 2003-03-06 CN CNA038048752A patent/CN1738806A/zh active Pending
- 2003-03-06 EA EA200401053A patent/EA200401053A1/ru unknown
- 2003-03-06 IL IL16381803A patent/IL163818A0/xx unknown
- 2003-03-06 BR BR0308280-6A patent/BR0308280A/pt not_active IP Right Cessation
- 2003-03-06 OA OA1200400234A patent/OA12782A/en unknown
- 2003-03-06 UY UY27700A patent/UY27700A1/es not_active Application Discontinuation
- 2003-03-06 AU AU2003212307A patent/AU2003212307A1/en not_active Abandoned
- 2003-03-06 MX MXPA04008681A patent/MXPA04008681A/es unknown
- 2003-03-06 PA PA20038568501A patent/PA8568501A1/es unknown
- 2003-03-06 KR KR10-2004-7013994A patent/KR20040095270A/ko not_active Ceased
- 2003-03-06 PL PL03372622A patent/PL372622A1/pl not_active Application Discontinuation
2004
- 2004-08-19 IS IS7414A patent/IS7414A/is unknown
- 2004-08-25 CO CO04082792A patent/CO5601020A2/es not_active Application Discontinuation
- 2004-08-31 MA MA27842A patent/MA27183A1/fr unknown
- 2004-09-03 EC EC2004005278A patent/ECSP045278A/es unknown
- 2004-09-03 TN TNP2004000169A patent/TNSN04169A1/fr unknown
- 2004-09-24 NO NO20044041A patent/NO20044041L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO20044041L (no)	2004-10-07
TNSN04169A1 (fr)	2007-03-12
WO2003076416A1 (en)	2003-09-18
ECSP045278A (es)	2004-10-26
MA27183A1 (fr)	2005-01-03
MXPA04008681A (es)	2004-12-06
KR20040095270A (ko)	2004-11-12
PL372622A1 (pl)	2005-07-25
IL163818A0 (en)	2005-12-18
AP2004003125A0 (en)	2004-09-30
EA200401053A1 (ru)	2005-04-28
IS7414A (is)	2004-08-19
AU2002249275A1 (en)	2003-09-22
EP1492775A2 (en)	2005-01-05
PE20031018A1 (es)	2004-01-09
AU2003212307A1 (en)	2003-09-22
CN1738806A (zh)	2006-02-22
JP2005526070A (ja)	2005-09-02
BR0308280A (pt)	2004-12-28
AR039562A1 (es)	2005-02-23
UY27700A1 (es)	2003-10-31
PA8568501A1 (es)	2003-12-19
SV2003001495A (es)	2003-11-04
WO2003076417A2 (en)	2003-09-18
CO5601020A2 (es)	2006-01-31
CA2478706A1 (en)	2003-09-18
WO2003076417A3 (en)	2003-11-13

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US5430148A (en)	1995-07-04	Antiproliferative quinazolines
US20030216402A1 (en)	2003-11-20	Oxo-azabicyclic compounds
US6747147B2 (en)	2004-06-08	Oxo-azabicyclic compounds
EP1492775A2 (en)	2005-01-05	Oxo-azabicyclic compounds
OA10703A (en)	2002-11-28	Quinoline and quinazoline compounds useful in therapy.
CN101970416A (zh)	2011-02-09	制备喹唑啉酮衍生物的方法
CA2658362A1 (en)	2008-01-03	Metalloprotease inhibitors
BG63777B1 (bg)	2002-12-29	Ароматни съединения и фармацевтични състави, които ги съдържат
CA2550717A1 (en)	2005-07-21	Bicycloheteroarylamine compounds as ion channel ligands and uses thereof
EP3624804A1 (en)	2020-03-25	Histone deacetylases (hdacs) inhibitors
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MXPA05011103A (es)	2005-12-12	Compuestos de quinazolina.
CA2236239C (en)	2003-03-18	Quinoline and quinazoline compounds useful in therapy
JP2002037787A (ja)	2002-02-06	［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体の製造法
ES2207277T3 (es)	2004-05-16	Compuestos utiles como inhibidores de aircraft.
US5574039A (en)	1996-11-12	Antiproliferative compounds having nitrogen-containing tricyclic ring systems and phenyl substituents
TW202239409A (zh)	2022-10-16	化合物
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