UA80578C2 - Pyridopyrimidinone compounds, method of their obtaining and pharmaceutical formulation that comprises them. - Google Patents

Pyridopyrimidinone compounds, method of their obtaining and pharmaceutical formulation that comprises them. Download PDF

Info

Publication number: UA80578C2
Authority: UA; Ukraine
Prior art keywords: group; formula; dipropylamino; pharmaceutically acceptable; compounds
Prior art date: 2002-11-05

Application number

UAA200505315A

Other languages

English (en)

Ukrainian (uk)

Inventor

Daniel-Henry Keniard

Bruno Pfeiffer

Pierre Renard

Original Assignee

Servier Lab

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.)

2002-11-05

Filing date

2003-04-11

Publication date

2007-10-10

2003-04-11 Application filed by Servier Lab filed Critical Servier Lab

2007-10-10 Publication of UA80578C2 publication Critical patent/UA80578C2/uk

Links

238000000034 method Methods 0.000 title claims description 25
239000008194 pharmaceutical composition Substances 0.000 title claims description 11
IAAQUOVTPAMQCR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-2-one Chemical class C1=CC=C2NC(=O)N=CC2=N1 IAAQUOVTPAMQCR-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 66
150000003839 salts Chemical class 0.000 claims abstract description 20
239000002253 acid Substances 0.000 claims abstract description 19
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 claims abstract description 14
206010028980 Neoplasm Diseases 0.000 claims abstract description 5
208000008589 Obesity Diseases 0.000 claims abstract description 5
201000011510 cancer Diseases 0.000 claims abstract description 5
235000020824 obesity Nutrition 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 17
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
239000000654 additive Substances 0.000 claims description 12
230000000996 additive effect Effects 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000006684 polyhaloalkyl group Polymers 0.000 claims description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
230000002526 effect on cardiovascular system Effects 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
MDKHWJFKHDRFFZ-UHFFFAOYSA-N 3,5-dimethylmorpholine Chemical compound CC1COCC(C)N1 MDKHWJFKHDRFFZ-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 5
239000003814 drug Substances 0.000 claims 5
230000002265 prevention Effects 0.000 claims 3
208000037849 arterial hypertension Diseases 0.000 claims 1
125000002785 azepinyl group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
108091000080 Phosphotransferase Proteins 0.000 abstract description 4
206010012601 diabetes mellitus Diseases 0.000 abstract description 4
102000020233 phosphotransferase Human genes 0.000 abstract description 4
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
102000001253 Protein Kinase Human genes 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
108060006633 protein kinase Proteins 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000012216 screening Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
KKCMJGDVCLWFQN-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrido[3,2-e][1,4]diazepin-3-amine Chemical compound C1NC(N)CNC2=CC=CN=C21 KKCMJGDVCLWFQN-UHFFFAOYSA-N 0.000 description 1
MDJRLHWRUFPGLL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)pyridin-3-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC=CC=C1N MDJRLHWRUFPGLL-UHFFFAOYSA-N 0.000 description 1
MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 1
DPASXGNZPSLEBK-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyridin-3-amine Chemical compound NC1=CC=CN=C1N1CCCC1 DPASXGNZPSLEBK-UHFFFAOYSA-N 0.000 description 1
VRRQBHZPUKCMJA-UHFFFAOYSA-N 2-thiomorpholin-4-ylpyridin-3-amine Chemical compound NC1=CC=CN=C1N1CCSCC1 VRRQBHZPUKCMJA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
208000032928 Dyslipidaemia Diseases 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010022489 Insulin Resistance Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000017170 Lipid metabolism disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 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
229960002523 mercuric chloride Drugs 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
229960003105 metformin Drugs 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229940100445 wheat starch Drugs 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

UAA200505315A 2002-11-05 2003-04-11 Pyridopyrimidinone compounds, method of their obtaining and pharmaceutical formulation that comprises them. UA80578C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0213804A FR2846657B1 (fr)	2002-11-05	2002-11-05	Nouveaux composes pyridopyrimidinone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
PCT/FR2003/003274 WO2004043956A1 (fr)	2002-11-05	2003-11-04	Composes pyridopyrimidinone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
UA80578C2 true UA80578C2 (en)	2007-10-10

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UAA200505315A UA80578C2 (en)	2002-11-05	2003-04-11	Pyridopyrimidinone compounds, method of their obtaining and pharmaceutical formulation that comprises them.

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US (1)	US7361662B2 (no)
EP (1)	EP1560826B1 (no)
JP (1)	JP2006512317A (no)
KR (1)	KR100717489B1 (no)
CN (1)	CN1330650C (no)
AR (1)	AR041883A1 (no)
AT (1)	ATE323092T1 (no)
AU (1)	AU2003292320B2 (no)
BR (1)	BR0315801A (no)
CA (1)	CA2503995A1 (no)
CY (1)	CY1105047T1 (no)
DE (1)	DE60304599T2 (no)
DK (1)	DK1560826T3 (no)
EA (1)	EA009043B1 (no)
ES (1)	ES2261978T3 (no)
FR (1)	FR2846657B1 (no)
GE (1)	GEP20084376B (no)
HK (1)	HK1081965A1 (no)
MA (1)	MA27410A1 (no)
MX (1)	MXPA05004789A (no)
MY (1)	MY140164A (no)
NO (1)	NO20052683D0 (no)
NZ (1)	NZ539598A (no)
PL (1)	PL376399A1 (no)
PT (1)	PT1560826E (no)
UA (1)	UA80578C2 (no)
WO (1)	WO2004043956A1 (no)
ZA (1)	ZA200503233B (no)

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CN101531638B (zh) *	2008-03-13	2011-12-28	中国科学院广州生物医药与健康研究院	用作***相关受体调节剂的化合物及其应用
CN101619063B (zh) *	2009-06-02	2011-08-10	华中师范大学	具有抗肿瘤活性的3,7,8-多取代吡啶并[4,3-d]嘧啶衍生物及制备
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PL2467387T3 (pl)	2009-08-20	2015-08-31	Karus Therapeutics Ltd	Tricykliczne związki heterocykliczne jako inhibitory kinazy 3-fosfoinozytydu
GB201204125D0 (en)	2012-03-08	2012-04-25	Karus Therapeutics Ltd	Compounds
EA030253B1 (ru)	2012-09-28	2018-07-31	Кэнсэр Ресерч Текнолоджи Лимитед	Азахиназолиновые ингибиторы атипичной протеинкиназы c
GB201402431D0 (en)	2014-02-12	2014-03-26	Karus Therapeutics Ltd	Compounds
WO2016068580A2 (en)	2014-10-29	2016-05-06	Dong-A Socio Holdings Co., Ltd.	Novel pyridopyrimidinone compounds for modulating the catalytic activity of histone lysine demethylases (kdms)
GB201514751D0 (en)	2015-08-19	2015-09-30	Karus Therapeutics Ltd	Compounds
GB201514754D0 (en)	2015-08-19	2015-09-30	Karus Therapeutics Ltd	Compounds
GB201514760D0 (en)	2015-08-19	2015-09-30	Karus Therapeutics Ltd	Compounds and method of use
GB201514758D0 (en)	2015-08-19	2015-09-30	Karus Therapeutics Ltd	Formulation
US20170057955A1 (en) *	2015-08-26	2017-03-02	Dong-A Socio Holdings Co., Ltd.	Pyridopyrimidinone Compounds for Modulating the Catalytic Activity of Histone Lysine Demethylases (KDMs)
CN105616420A (zh) *	2016-01-16	2016-06-01	赵国良	一种降血脂的药物组合物
IL277071B1 (en)	2018-03-08	2024-03-01	Incyte Corp	Aminopyrizine diol compounds as PI3K–y inhibitors
US11046658B2 (en)	2018-07-02	2021-06-29	Incyte Corporation	Aminopyrazine derivatives as PI3K-γ inhibitors
WO2021102288A1 (en) *	2019-11-22	2021-05-27	Senda Biosciences, Inc.	Pyridopyrimidinone derivatives as ahr antagonists
WO2024008722A2 (en) *	2022-07-04	2024-01-11	Muna Therapeutics Aps	Trem2 modulators

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2002
- 2002-11-05 FR FR0213804A patent/FR2846657B1/fr not_active Expired - Fee Related
2003
- 2003-04-11 UA UAA200505315A patent/UA80578C2/uk unknown
- 2003-10-09 MY MYPI20033854A patent/MY140164A/en unknown
- 2003-11-04 JP JP2004550726A patent/JP2006512317A/ja active Pending
- 2003-11-04 AR ARP030104026A patent/AR041883A1/es unknown
- 2003-11-04 US US10/533,697 patent/US7361662B2/en not_active Expired - Fee Related
- 2003-11-04 CA CA002503995A patent/CA2503995A1/fr not_active Abandoned
- 2003-11-04 WO PCT/FR2003/003274 patent/WO2004043956A1/fr active IP Right Grant
- 2003-11-04 EA EA200500690A patent/EA009043B1/ru not_active IP Right Cessation
- 2003-11-04 BR BR0315801-2A patent/BR0315801A/pt not_active IP Right Cessation
- 2003-11-04 MX MXPA05004789A patent/MXPA05004789A/es active IP Right Grant
- 2003-11-04 ES ES03767886T patent/ES2261978T3/es not_active Expired - Lifetime
- 2003-11-04 AU AU2003292320A patent/AU2003292320B2/en not_active Expired - Fee Related
- 2003-11-04 KR KR1020057007994A patent/KR100717489B1/ko not_active IP Right Cessation
- 2003-11-04 DK DK03767886T patent/DK1560826T3/da active
- 2003-11-04 EP EP03767886A patent/EP1560826B1/fr not_active Expired - Lifetime
- 2003-11-04 PL PL03376399A patent/PL376399A1/xx not_active Application Discontinuation
- 2003-11-04 GE GEAP20038824A patent/GEP20084376B/en unknown
- 2003-11-04 CN CNB2003801027139A patent/CN1330650C/zh not_active Expired - Fee Related
- 2003-11-04 PT PT03767886T patent/PT1560826E/pt unknown
- 2003-11-04 NZ NZ539598A patent/NZ539598A/en unknown
- 2003-11-04 DE DE60304599T patent/DE60304599T2/de not_active Expired - Fee Related
- 2003-11-04 AT AT03767886T patent/ATE323092T1/de not_active IP Right Cessation
2005
- 2005-04-19 MA MA28232A patent/MA27410A1/fr unknown
- 2005-04-21 ZA ZA200503233A patent/ZA200503233B/en unknown
- 2005-06-03 NO NO20052683A patent/NO20052683D0/no not_active Application Discontinuation
2006
- 2006-02-22 HK HK06102331A patent/HK1081965A1/xx not_active IP Right Cessation
- 2006-06-08 CY CY20061100767T patent/CY1105047T1/el unknown

Also Published As

Publication number	Publication date
EP1560826A1 (fr)	2005-08-10
KR20050087792A (ko)	2005-08-31
EA200500690A1 (ru)	2005-10-27
MA27410A1 (fr)	2005-06-01
US7361662B2 (en)	2008-04-22
CN1711260A (zh)	2005-12-21
EA009043B1 (ru)	2007-10-26
FR2846657A1 (fr)	2004-05-07
ATE323092T1 (de)	2006-04-15
PT1560826E (pt)	2006-07-31
CY1105047T1 (el)	2009-11-04
EP1560826B1 (fr)	2006-04-12
NZ539598A (en)	2006-11-30
HK1081965A1 (en)	2006-05-26
DK1560826T3 (da)	2006-08-14
US20050288311A1 (en)	2005-12-29
BR0315801A (pt)	2005-09-20
WO2004043956A8 (fr)	2005-06-09
KR100717489B1 (ko)	2007-05-14
ZA200503233B (en)	2006-06-28
PL376399A1 (en)	2005-12-27
DE60304599D1 (de)	2006-05-24
WO2004043956A1 (fr)	2004-05-27
NO20052683L (no)	2005-06-03
AR041883A1 (es)	2005-06-01
MXPA05004789A (es)	2005-07-22
ES2261978T3 (es)	2006-11-16
FR2846657B1 (fr)	2004-12-24
AU2003292320B2 (en)	2009-03-12
JP2006512317A (ja)	2006-04-13
GEP20084376B (en)	2008-05-27
MY140164A (en)	2009-11-30
AU2003292320A1 (en)	2004-06-03
CN1330650C (zh)	2007-08-08
NO20052683D0 (no)	2005-06-03
CA2503995A1 (fr)	2004-05-27
DE60304599T2 (de)	2007-05-16

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