TWI260324B - Thiazolopyrimidinone compounds, process for preparing the same, and pharmaceutical composition comprising the same - Google Patents
Thiazolopyrimidinone compounds, process for preparing the same, and pharmaceutical composition comprising the same Download PDFInfo
- Publication number
- TWI260324B TWI260324B TW089121952A TW89121952A TWI260324B TW I260324 B TWI260324 B TW I260324B TW 089121952 A TW089121952 A TW 089121952A TW 89121952 A TW89121952 A TW 89121952A TW I260324 B TWI260324 B TW I260324B
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- amino
- thio
- pyrimidin
- pyrimidine
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- AKDQOJPOLRMVMF-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine 3-oxide Chemical class N1=CN=C2S(=O)C=NC2=C1 AKDQOJPOLRMVMF-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 144
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 242
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 241
- -1 -OR4 Chemical group 0.000 claims description 162
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 142
- 150000001875 compounds Chemical class 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 61
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- 102000004127 Cytokines Human genes 0.000 claims description 12
- 108090000695 Cytokines Proteins 0.000 claims description 12
- 159000000000 sodium salts Chemical class 0.000 claims description 12
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 11
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
- 150000003573 thiols Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
- DCSLKYLPOSSKFY-UHFFFAOYSA-N 3h-[1,3]thiazolo[4,5-d]pyrimidin-2-one Chemical compound C1=NC=C2SC(=O)NC2=N1 DCSLKYLPOSSKFY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 52
- 239000004305 biphenyl Substances 0.000 claims 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims 1
- ILQCMTVABGAPII-UHFFFAOYSA-N 3h-[1,3]oxazolo[4,5-d]pyrimidin-2-one Chemical compound C1=NC=C2OC(=O)NC2=N1 ILQCMTVABGAPII-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims 1
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- 206010028980 Neoplasm Diseases 0.000 claims 1
- LNVWKEXPRCZTSC-UHFFFAOYSA-N [Na].S1C(NC=2N=CN=CC21)=O Chemical compound [Na].S1C(NC=2N=CN=CC21)=O LNVWKEXPRCZTSC-UHFFFAOYSA-N 0.000 claims 1
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- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 40
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
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- 101150041968 CDC13 gene Proteins 0.000 description 13
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- 238000007792 addition Methods 0.000 description 9
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- MTVUEWBUJJLDPS-UHFFFAOYSA-N 1h-pyrimidin-2-one;dihydrochloride Chemical compound Cl.Cl.O=C1N=CC=CN1 MTVUEWBUJJLDPS-UHFFFAOYSA-N 0.000 description 7
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
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- 238000012856 packing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
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- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 description 1
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- 230000007958 sleep Effects 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- MOZOQDNRVPHFOO-RNFRBKRXSA-N tert-butyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](N)[C@H](O)C1 MOZOQDNRVPHFOO-RNFRBKRXSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—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
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
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- 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
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- 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
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9903544A SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI260324B true TWI260324B (en) | 2006-08-21 |
Family
ID=20417218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089121952A TWI260324B (en) | 1999-10-01 | 2000-10-19 | Thiazolopyrimidinone compounds, process for preparing the same, and pharmaceutical composition comprising the same |
Country Status (26)
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| EP (2) | EP1348709B1 (enExample) |
| JP (1) | JP4824889B2 (enExample) |
| KR (1) | KR100765051B1 (enExample) |
| CN (1) | CN1210279C (enExample) |
| AT (2) | ATE257838T1 (enExample) |
| AU (1) | AU777872B2 (enExample) |
| BR (1) | BR0014334A (enExample) |
| CA (1) | CA2385269C (enExample) |
| CZ (1) | CZ20021113A3 (enExample) |
| DE (2) | DE60037836T2 (enExample) |
| DK (1) | DK1222195T3 (enExample) |
| EE (1) | EE05037B1 (enExample) |
| ES (2) | ES2213043T3 (enExample) |
| HU (1) | HUP0204246A3 (enExample) |
| IL (2) | IL148910A0 (enExample) |
| IS (1) | IS2229B (enExample) |
| MX (1) | MXPA02003263A (enExample) |
| NO (1) | NO327706B1 (enExample) |
| NZ (1) | NZ517880A (enExample) |
| PT (1) | PT1222195E (enExample) |
| SE (1) | SE9903544D0 (enExample) |
| TW (1) | TWI260324B (enExample) |
| UA (1) | UA73521C2 (enExample) |
| WO (1) | WO2001025242A1 (enExample) |
| ZA (1) | ZA200202380B (enExample) |
Families Citing this family (33)
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| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| DE60101372T2 (de) * | 2000-02-11 | 2004-10-14 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
| GB2359081A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
| GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359551A (en) * | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| SE0003828D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Novel compounds |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| SE0102716D0 (sv) * | 2001-08-14 | 2001-08-14 | Astrazeneca Ab | Novel compounds |
| AU2002351183B2 (en) | 2001-12-06 | 2008-05-08 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| AU2002363960B2 (en) | 2001-12-06 | 2008-07-10 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| GB0217431D0 (en) * | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| DE60304718T2 (de) | 2002-08-06 | 2007-04-26 | Astrazeneca Ab | Kondensierte pyridine und pyrimidine mit tie2 (tek) aktivität |
| DE60318219T2 (de) | 2002-08-24 | 2009-01-15 | Astrazeneca Ab | PYRIMIDINDERIVATE ALS MODULATOREN DER AKTIVITuT VON CHEMOKINREZEPTOREN |
| GB0221828D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| JP2007507494A (ja) * | 2003-10-07 | 2007-03-29 | アストラゼネカ・アクチエボラーグ | ケモカイン受容体アンタゴニストとりわけＣＸ３ＣＲ１として有用な新規な２−置換４−アミノ−チアゾロ［４，５−ｄ］ピリミジン |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| BRPI0514735B8 (pt) | 2004-08-28 | 2021-05-25 | Astrazeneca Ab | derivados de pirimidino sulfonamida como moduladores do receptor de quimiocina. |
| WO2006064228A2 (en) * | 2004-12-17 | 2006-06-22 | Astrazeneca Ab | Thiazolopyramidine compounds for the modulation of chemokine receptor activity |
| WO2006101439A1 (en) * | 2005-03-23 | 2006-09-28 | Astrazeneca Ab | Screen |
| AR053347A1 (es) * | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
| UA90707C2 (en) * | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| TW200820973A (en) | 2006-09-29 | 2008-05-16 | Astrazeneca Ab | Novel compounds 480 |
| AR071036A1 (es) * | 2008-03-26 | 2010-05-19 | Astrazeneca Ab | Derivados 5, 7-disustituidos de [1, 3]tiazolo[4, 5-d]pirimidin-2 (3h)-ona, una composicion farmaceutica que los comprende y su uso en el tratamiento de enfermedades mediadas por el receptor cx3cr1. |
| CN101671336B (zh) | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
| CN101899058B (zh) * | 2010-05-24 | 2012-05-23 | 中国人民解放军第四军医大学 | 一种噻唑并嘧啶化合物及其制备方法和应用 |
| WO2014205127A2 (en) | 2013-06-18 | 2014-12-24 | New York University | Cellular factors involved in the cytotoxicity of staphylococcus aureus leukocidins: novel therapeutic targets |
| US10561676B2 (en) | 2013-08-02 | 2020-02-18 | Syntrix Biosystems Inc. | Method for treating cancer using dual antagonists of CXCR1 and CXCR2 |
| CA2920172C (en) * | 2013-08-02 | 2020-03-10 | Syntrix Biosystems, Inc. | 2- [5- [n- (4-fluorophenyl) carbamoyl] pyrimidin-2-ylsulfanylmethyl] -4- (trifluoromethoxy) phenyl] boronic acid |
| US8969365B2 (en) | 2013-08-02 | 2015-03-03 | Syntrix Biosystems, Inc. | Thiopyrimidinecarboxamides as CXCR1/2 modulators |
| US10046002B2 (en) | 2013-08-02 | 2018-08-14 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| WO2018073248A1 (en) | 2016-10-17 | 2018-04-26 | Icm (Institut Du Cerveau Et De La Moelle Épinière) | Prognosis of demyelinating diseases patients and treatment thereof |
| CN110172067B (zh) * | 2019-04-11 | 2021-06-15 | 河南科技大学第一附属医院 | 一种具有杀菌活性的噻唑类药物分子及其制备方法 |
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| US2924472A (en) | 1957-06-27 | 1960-02-09 | Gen Motors Corp | Pipe joint seal |
| US3182062A (en) | 1962-02-28 | 1965-05-04 | Smith Kline French Lab | Synthesis of quinoxalines and analogues thereof |
| GB1009477A (en) | 1962-02-13 | 1965-11-10 | Smith Kline French Lab | Novel process for preparing heterocyclic compounds |
| US3318900A (en) | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| BE668603A (enExample) | 1964-08-20 | |||
| DE2331223C2 (de) | 1972-06-19 | 1984-11-22 | Kohjin Co., Ltd., Tokio / Tokyo | S-substituierte-2-Thioadenosine, deren 5'-Monophosphate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| US4120521A (en) | 1975-08-28 | 1978-10-17 | Rieber & Son Plastic-Industri A/S | Combined mould element and sealing ring |
| EG12406A (en) | 1976-08-12 | 1979-03-31 | Janssen Pharmaceutica Nv | Process for preparing of novel n-aryl-n-(1-l-4-piperidinyl)-arylacetamides |
| GB1600293A (en) | 1977-02-04 | 1981-10-14 | British Oceanics Ltd | Sealing arrangements |
| US4188040A (en) | 1977-04-06 | 1980-02-12 | Firma WOCO Franz-Josef Wolf & Co. | Sealing ring |
| DE2726959A1 (de) | 1977-06-15 | 1979-01-18 | Arlt Christian | Dichteinsatz zum dichten verbinden von zwei rohren |
| FR2421899A1 (fr) | 1978-01-16 | 1979-11-02 | Roussel Uclaf | Nouveaux derives du tetrahydropyridinyl-indole et leurs sels, le procede de preparation et l'application a titre de medicaments de ces nouveaux produits |
| US4410528A (en) | 1980-05-16 | 1983-10-18 | Kyowa Hakko Kogyo Co., Ltd. | Hypotensive piperidine derivatives |
| DE3219522A1 (de) | 1981-10-28 | 1983-12-01 | Denso-Chemie Wedekind Kg, 5090 Leverkusen | Steckmuffendichtung fuer rohre |
| FR2547888B1 (fr) | 1983-06-22 | 1985-12-13 | Sabla Sa | Bague d'etancheite a implants pour tuyaux a emboitement |
| CA1338012C (en) | 1987-04-27 | 1996-01-30 | John Michael Mccall | Pharmaceutically active amines |
| SE8800348L (sv) | 1988-02-03 | 1989-08-04 | Forsheda Ab | Taetningsring och verktyg foer framstaellning daerav |
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