ZA200503233B - Pyridopyrimidinone compounds, method for production thereof and medicaments comprising the same - Google Patents
Pyridopyrimidinone compounds, method for production thereof and medicaments comprising the same Download PDFInfo
- Publication number
- ZA200503233B ZA200503233B ZA200503233A ZA200503233A ZA200503233B ZA 200503233 B ZA200503233 B ZA 200503233B ZA 200503233 A ZA200503233 A ZA 200503233A ZA 200503233 A ZA200503233 A ZA 200503233A ZA 200503233 B ZA200503233 B ZA 200503233B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrido
- pyrimidin
- group
- formula
- dipropylamino
- Prior art date
Links
- 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
- 239000003814 drug Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- QMOPAFMMLWUTKI-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(O)=NC=NC2=C1 QMOPAFMMLWUTKI-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 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 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 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
- 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
- RSIMDORWABAIMD-UHFFFAOYSA-N 2-(dipropylamino)-8-pyrrolidin-1-yl-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(=O)NC(N(CCC)CCC)=NC2=C1N1CCCC1 RSIMDORWABAIMD-UHFFFAOYSA-N 0.000 claims description 3
- NIJFCTBJZSRTEV-UHFFFAOYSA-N 2-(dipropylamino)-8-thiomorpholin-4-yl-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(=O)NC(N(CCC)CCC)=NC2=C1N1CCSCC1 NIJFCTBJZSRTEV-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 3
- XOCYRXFIIHFDIJ-UHFFFAOYSA-N 8-(azepan-1-yl)-2-(dipropylamino)-6-morpholin-4-yl-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1=C2C(=O)NC(N(CCC)CCC)=NC2=C(N2CCCCCC2)N=C1N1CCOCC1 XOCYRXFIIHFDIJ-UHFFFAOYSA-N 0.000 claims description 3
- JXVDLPWVRORNQJ-UHFFFAOYSA-N 8-(azocan-1-yl)-2-(dipropylamino)-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(=O)NC(N(CCC)CCC)=NC2=C1N1CCCCCCC1 JXVDLPWVRORNQJ-UHFFFAOYSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002785 azepinyl group Chemical group 0.000 claims description 3
- 201000011510 cancer Diseases 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
- 230000001419 dependent effect Effects 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- MWCUXCNAXIQCQW-UHFFFAOYSA-N 2-amino-8-(azepan-1-yl)-6-morpholin-4-yl-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1=C2C(=O)NC(N)=NC2=C(N2CCCCCC2)N=C1N1CCOCC1 MWCUXCNAXIQCQW-UHFFFAOYSA-N 0.000 claims description 2
- IQJMXNUPHCQRSJ-UHFFFAOYSA-N 6,8-bis(azepan-1-yl)-2-(dipropylamino)-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1=C2C(=O)NC(N(CCC)CCC)=NC2=C(N2CCCCCC2)N=C1N1CCCCCC1 IQJMXNUPHCQRSJ-UHFFFAOYSA-N 0.000 claims description 2
- RTUHGFCRBLVTGT-UHFFFAOYSA-N 8-(3,4-dimethoxyphenyl)-2-(dipropylamino)-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(=O)NC(N(CCC)CCC)=NC2=C1C1=CC=C(OC)C(OC)=C1 RTUHGFCRBLVTGT-UHFFFAOYSA-N 0.000 claims description 2
- KZRYXBGNLRRUBB-UHFFFAOYSA-N 8-(azepan-1-yl)-2,6-dimorpholin-4-yl-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound C1=C2C(=O)NC(N3CCOCC3)=NC2=C(N2CCCCCC2)N=C1N1CCOCC1 KZRYXBGNLRRUBB-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
- 102000004877 Insulin Human genes 0.000 claims description 2
- 108090001061 Insulin Proteins 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 208000037849 arterial hypertension Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229940125396 insulin Drugs 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
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 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 2
- NWTYIYRGSWZFPG-UHFFFAOYSA-N 8-chloro-2-(dipropylamino)-1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(=O)NC(N(CCC)CCC)=NC2=C1Cl NWTYIYRGSWZFPG-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 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 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- 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
- 238000011282 treatment Methods 0.000 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- 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
- 102000001253 Protein Kinase Human genes 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-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
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 108060006633 protein kinase Proteins 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent 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
- 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
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate 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
- 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
- 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
- 230000002500 effect on skin Effects 0.000 description 1
- RAMWAPBGTMMDSI-UHFFFAOYSA-N ethyl n-(diaminomethylidene)carbamate Chemical compound CCOC(=O)NC(N)=N RAMWAPBGTMMDSI-UHFFFAOYSA-N 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
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 208000030159 metabolic disease Diseases 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
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503233B true ZA200503233B (en) | 2006-06-28 |
Family
ID=32104442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503233A ZA200503233B (en) | 2002-11-05 | 2005-04-21 | Pyridopyrimidinone compounds, method for production thereof and medicaments comprising the same |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7361662B2 (ja) |
| EP (1) | EP1560826B1 (ja) |
| JP (1) | JP2006512317A (ja) |
| KR (1) | KR100717489B1 (ja) |
| CN (1) | CN1330650C (ja) |
| AR (1) | AR041883A1 (ja) |
| AT (1) | ATE323092T1 (ja) |
| AU (1) | AU2003292320B2 (ja) |
| BR (1) | BR0315801A (ja) |
| CA (1) | CA2503995A1 (ja) |
| CY (1) | CY1105047T1 (ja) |
| DE (1) | DE60304599T2 (ja) |
| DK (1) | DK1560826T3 (ja) |
| EA (1) | EA009043B1 (ja) |
| ES (1) | ES2261978T3 (ja) |
| FR (1) | FR2846657B1 (ja) |
| GE (1) | GEP20084376B (ja) |
| HK (1) | HK1081965A1 (ja) |
| MA (1) | MA27410A1 (ja) |
| MX (1) | MXPA05004789A (ja) |
| MY (1) | MY140164A (ja) |
| NO (1) | NO20052683L (ja) |
| NZ (1) | NZ539598A (ja) |
| PL (1) | PL376399A1 (ja) |
| PT (1) | PT1560826E (ja) |
| UA (1) | UA80578C2 (ja) |
| WO (1) | WO2004043956A1 (ja) |
| ZA (1) | ZA200503233B (ja) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009003673A (es) * | 2006-10-04 | 2009-04-22 | Pfizer Prod Inc | Derivados de piridido[4,3-d]pirimidin-4(3h)-ona como antagonistas de los receptores de calcio. |
| 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 | 用作雌激素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 |
| US8981087B2 (en) | 2009-07-29 | 2015-03-17 | Karus Therapeutics Limited | Benzo [E] [1,3] oxazin-4-one derivatives as phosphoinositide 3-kinase inhibitors |
| CA2771594C (en) | 2009-08-20 | 2018-05-01 | Karus Therapeutics Limited | Tricyclic heterocyclic compounds as phosphoinositide 3-kinase inhibitors |
| GB201204125D0 (en) | 2012-03-08 | 2012-04-25 | Karus Therapeutics Ltd | Compounds |
| JP6535430B2 (ja) | 2012-09-28 | 2019-06-26 | イグニタ、インク． | 非定型プロテインキナーゼｃのアザキナゾリン阻害薬 |
| GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
| CA2962917C (en) | 2014-10-29 | 2019-04-30 | Dong-A St Co., Ltd. | Novel pyridopyrimidinone compounds for modulating the catalytic activity of histone lysine demethylases (kdms) |
| 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 |
| GB201514751D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds |
| 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 |
| WO2019226213A2 (en) | 2018-03-08 | 2019-11-28 | Incyte Corporation | AMINOPYRAZINE DIOL COMPOUNDS AS PI3K-y INHIBITORS |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| MX2022006086A (es) * | 2019-11-22 | 2022-09-07 | Senda Biosciences Inc | Derivados de piridopirimidinona como antagonistas de ahr. |
| WO2024008722A2 (en) * | 2022-07-04 | 2024-01-11 | Muna Therapeutics Aps | Trem2 modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6348310B1 (en) * | 1994-03-04 | 2002-02-19 | Promega Corporation | Quantitation of individual protein kinase activity |
| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
| ZA9756B (en) * | 1996-01-16 | 1997-07-17 | Warner Lambert Co | Process for preparing 4,6-disubstituted pyrido[3,4-d]-pyrimidines |
| HRP970371A2 (en) * | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| CN1093130C (zh) * | 1996-08-06 | 2002-10-23 | 辉瑞大药厂 | 被取代的吡啶并6,6－二环衍生物 |
| US6962922B2 (en) * | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| AUPS019702A0 (en) * | 2002-01-29 | 2002-02-21 | Fujisawa Pharmaceutical Co., Ltd. | Condensed heterocyclic compounds |
-
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 AT AT03767886T patent/ATE323092T1/de not_active IP Right Cessation
- 2003-11-04 JP JP2004550726A patent/JP2006512317A/ja active Pending
- 2003-11-04 AU AU2003292320A patent/AU2003292320B2/en not_active Expired - Fee Related
- 2003-11-04 DK DK03767886T patent/DK1560826T3/da active
- 2003-11-04 CA CA002503995A patent/CA2503995A1/fr not_active Abandoned
- 2003-11-04 ES ES03767886T patent/ES2261978T3/es not_active Expired - Lifetime
- 2003-11-04 EA EA200500690A patent/EA009043B1/ru not_active IP Right Cessation
- 2003-11-04 PL PL03376399A patent/PL376399A1/xx not_active Application Discontinuation
- 2003-11-04 CN CNB2003801027139A patent/CN1330650C/zh not_active Expired - Fee Related
- 2003-11-04 US US10/533,697 patent/US7361662B2/en not_active Expired - Fee Related
- 2003-11-04 GE GEAP20038824A patent/GEP20084376B/en unknown
- 2003-11-04 DE DE60304599T patent/DE60304599T2/de not_active Expired - Fee Related
- 2003-11-04 BR BR0315801-2A patent/BR0315801A/pt not_active IP Right Cessation
- 2003-11-04 WO PCT/FR2003/003274 patent/WO2004043956A1/fr active IP Right Grant
- 2003-11-04 PT PT03767886T patent/PT1560826E/pt unknown
- 2003-11-04 AR ARP030104026A patent/AR041883A1/es unknown
- 2003-11-04 EP EP03767886A patent/EP1560826B1/fr not_active Expired - Lifetime
- 2003-11-04 MX MXPA05004789A patent/MXPA05004789A/es active IP Right Grant
- 2003-11-04 KR KR1020057007994A patent/KR100717489B1/ko not_active IP Right Cessation
- 2003-11-04 NZ NZ539598A patent/NZ539598A/en unknown
-
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/NO20052683L/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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200503233B (en) | Pyridopyrimidinone compounds, method for production thereof and medicaments comprising the same | |
| EP0182165B1 (en) | Thienyl condensed-pyrazole derivatives | |
| US5091384A (en) | Anti-bacterial quinolone- and naphthyridone-carboxylic acid compounds | |
| WO2007129111A1 (en) | Diazepine derivatives as 5-ht2a antagonists | |
| MXPA04009318A (es) | Derivados de quinolina y su uso como ligados 5-ht6. | |
| EP0608897A2 (en) | Tyrosine kinase inhibitors and benzoylacrylamide derivatives | |
| PL147392B1 (en) | Method of obtaining novel derivatives of 1,4-dihydronaphtidrine and their salts | |
| AU2002233706B2 (en) | Pyridopyrimidine or naphthyridine derivative | |
| HU198713B (en) | Process for producing ergolin derivatives and pharmaceutical compositions containing them as active components | |
| Araki et al. | Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships | |
| NZ280258A (en) | Quinoxaline derivatives; preparative method and medicaments | |
| EP0424851A1 (en) | Quinolone compounds and a process for their preparation | |
| US5191079A (en) | Quinolinecarboxylic acid derivatives | |
| JPH0616673A (ja) | ７−オキソ−７Ｈ−ピリド［１，２，３−ｄｅ［１，４ベンゾキサジン−６−カルボン酸類およびエステル類 | |
| IE913005A1 (en) | Indolonaphthyridines | |
| FI68823C (fi) | Foerfarande foer framstaellning av nya antibakteriella 2-amino-8-cyklopropyl-5-oxo-5,8-dihydro-pyrido(2,3-d)pyrimidin-6-karboxylsyror | |
| Ziegler Jr et al. | Synthesis and antibacterial activity of some 7‐substituted 1‐ethyl‐6‐fluoro‐1, 4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acids: Ethers, secondary amines and sulfides as c‐7 substituents | |
| FI82456C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1-fenyl-1,2,4-tiadiazin-1-oxidderivat. | |
| EP0277625A2 (en) | Tetrahydropyrido[3',4':4,5]pyrrolo[2,3-c]quinolines, intermediates and a process for the preparation thereof and their use as hypotensive agents | |
| CZ280594A3 (en) | Derivatives of 1-(2-fluorocyclopropyl)-quinolonecarboxylic acid and 1-(2-fluorocyclopropyl)-naphthyridonecarboxylic acid, process of their preparation and use in medicaments | |
| FI89480C (fi) | Foerfarande foer framstaellning av ett terapeutiskt aktivt aminderivat | |
| NZ328432A (en) | Tricyclic bis-imide derivatives and medicaments | |
| KR100359151B1 (ko) | 2환성 아미노기로 치환된 피리돈카르복실산 유도체, 그의 에스테르 및 그의 염 및 이들의 중간체인 2환성 아민 | |
| EP0175570A2 (en) | Process for the preparation of aromatic-1,4-oxazepinones and thiones | |
| CS245790B2 (cs) | Způsob výroby derivátů ergolinu |