FI106960B - Menetelmä terapeuttisesti aktiivisten 1-fenyyli-pyrido[2,3-d]pyrimidiini-2,4-dioni- ja 2-onijohdannaisten valmistamiseksi - Google Patents
Menetelmä terapeuttisesti aktiivisten 1-fenyyli-pyrido[2,3-d]pyrimidiini-2,4-dioni- ja 2-onijohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI106960B FI106960B FI944305A FI944305A FI106960B FI 106960 B FI106960 B FI 106960B FI 944305 A FI944305 A FI 944305A FI 944305 A FI944305 A FI 944305A FI 106960 B FI106960 B FI 106960B
- Authority
- FI
- Finland
- Prior art keywords
- pyrido
- pyrimidine
- dione
- formula
- pyridylmethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 89
- 238000002360 preparation method Methods 0.000 title claims description 75
- 230000008569 process Effects 0.000 title claims description 19
- IMHWTGUXZBPFDM-UHFFFAOYSA-N 1-phenylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C2=CC=CN=C2N1C1=CC=CC=C1 IMHWTGUXZBPFDM-UHFFFAOYSA-N 0.000 title description 6
- -1 pyridyl N-oxide Chemical group 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 144
- 238000006243 chemical reaction Methods 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 22
- QGKGASXQTBQINX-UHFFFAOYSA-N 3,4-dihydro-1h-pyrimidin-2-one Chemical compound O=C1NCC=CN1 QGKGASXQTBQINX-UHFFFAOYSA-N 0.000 claims description 21
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 18
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- JISZFRZDAXTJGT-UHFFFAOYSA-N methyl 3-[2,4-dioxo-3-(pyridin-3-ylmethyl)pyrido[2,3-d]pyrimidin-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C(N(CC=3C=NC=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 JISZFRZDAXTJGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- YLHRMVRLIOIWTO-UHFFFAOYSA-N 1-(3-nitrophenyl)-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(CC=3C=CN=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 YLHRMVRLIOIWTO-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- QTVKLFYTISVDOC-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound ClC1=CC=CC(N2C(N(CC=3C=CN=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 QTVKLFYTISVDOC-UHFFFAOYSA-N 0.000 claims description 4
- DAGZOMMSVOOPMS-UHFFFAOYSA-N 3-[2,4-dioxo-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidin-1-yl]benzonitrile Chemical compound O=C1C2=CC=CN=C2N(C=2C=C(C=CC=2)C#N)C(=O)N1CC1=CC=NC=C1 DAGZOMMSVOOPMS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- GMQNXISAYIRAFJ-UHFFFAOYSA-N 1-(3-nitrophenyl)-3-(pyridin-3-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(CC=3C=NC=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 GMQNXISAYIRAFJ-UHFFFAOYSA-N 0.000 claims description 3
- ROSFKXDQMBPYQQ-UHFFFAOYSA-N 1-(3-nitrophenyl)-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC(N2C(N(CC=3C=CN=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 ROSFKXDQMBPYQQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- SVRNPMAYXZNRHD-UHFFFAOYSA-N methyl 3-[2,4-dioxo-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidin-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C(N(CC=3C=CN=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 SVRNPMAYXZNRHD-UHFFFAOYSA-N 0.000 claims description 3
- UUDZSOQPKQTJPR-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(pyridin-4-ylmethyl)-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound ClC1=CC=CC(N2C3=NC=CC=C3CN(CC=3C=CN=CC=3)C2=O)=C1 UUDZSOQPKQTJPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- MBYULSWQNLZIAJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(pyridin-3-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound ClC1=CC=CC(N2C(N(CC=3C=NC=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 MBYULSWQNLZIAJ-UHFFFAOYSA-N 0.000 claims 2
- DCKMUXFLBIAEAH-UHFFFAOYSA-N 1-phenyl-3-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1C2=CC=CN=C2N(C=2C=CC=CC=2)C(=O)N1CC1=CC=NC=C1 DCKMUXFLBIAEAH-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- ALZKIYWRMWPNAN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(pyridin-3-ylmethyl)-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound ClC1=CC=CC(N2C3=NC=CC=C3CN(CC=3C=NC=CC=3)C2=O)=C1 ALZKIYWRMWPNAN-UHFFFAOYSA-N 0.000 claims 1
- TXLLMXXVURYZIR-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(pyridin-4-ylmethyl)-2,4-dihydropyrido[2,3-d]pyrimidine Chemical compound ClC1=CC=CC(N2C3=NC=CC=C3CN(CC=3C=CN=CC=3)C2)=C1 TXLLMXXVURYZIR-UHFFFAOYSA-N 0.000 claims 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 241000277284 Salvelinus fontinalis Species 0.000 claims 1
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- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 102000013370 fibrillin Human genes 0.000 claims 1
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- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
- 239000002904 solvent Substances 0.000 description 67
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
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- VYPPZXZHYDSBSJ-UHFFFAOYSA-N methyl 6-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C)N=C1 VYPPZXZHYDSBSJ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000002297 mitogenic effect Effects 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- SUJVKLGPMOZVMV-UHFFFAOYSA-N n-[3-(aminomethyl)pyridin-2-yl]-n-phenylnitramide Chemical compound NCC1=CC=CN=C1N([N+]([O-])=O)C1=CC=CC=C1 SUJVKLGPMOZVMV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000005375 negative regulation of lymphocyte activation Effects 0.000 description 1
- 229960003057 nialamide Drugs 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012279 sodium borohydride Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85517992 | 1992-03-20 | ||
| US07/855,179 US5264437A (en) | 1992-03-20 | 1992-03-20 | Optionally substituted pyrido[2,3-d]pyridine-2,4(1H,3H)-diones and pyrido[2,]pyrimidine-2(1H,3H)-ones |
| PCT/US1993/002273 WO1993019068A1 (en) | 1992-03-20 | 1993-03-18 | PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS |
| US9302273 | 1993-03-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944305L FI944305L (fi) | 1994-09-16 |
| FI944305A0 FI944305A0 (fi) | 1994-09-16 |
| FI106960B true FI106960B (fi) | 2001-05-15 |
Family
ID=25320543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI944305A FI106960B (fi) | 1992-03-20 | 1994-09-16 | Menetelmä terapeuttisesti aktiivisten 1-fenyyli-pyrido[2,3-d]pyrimidiini-2,4-dioni- ja 2-onijohdannaisten valmistamiseksi |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5264437A (OSRAM) |
| EP (2) | EP0631580A1 (OSRAM) |
| JP (1) | JP3241384B2 (OSRAM) |
| KR (1) | KR100274104B1 (OSRAM) |
| CN (1) | CN1040327C (OSRAM) |
| AU (1) | AU669520B2 (OSRAM) |
| CA (1) | CA2132297C (OSRAM) |
| FI (1) | FI106960B (OSRAM) |
| HU (2) | HUT67552A (OSRAM) |
| IL (1) | IL105092A (OSRAM) |
| MX (1) | MX9301530A (OSRAM) |
| NO (1) | NO301763B1 (OSRAM) |
| NZ (1) | NZ251525A (OSRAM) |
| TW (1) | TW240226B (OSRAM) |
| WO (1) | WO1993019068A1 (OSRAM) |
| ZA (1) | ZA931945B (OSRAM) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5672622A (en) * | 1994-04-21 | 1997-09-30 | Berlex Laboratories, Inc. | Treatment of multiple sclerosis |
| US6060501A (en) * | 1994-06-02 | 2000-05-09 | Schering Aktiengesellschaft | Combined treatment of multiple sclerosis |
| US5817670A (en) * | 1994-08-29 | 1998-10-06 | Yamanouchi Pharmaceutical Co., Ltd. | Naphthyridine derivatives and pharmaceutical compositions thereof |
| ZA961081B (en) * | 1995-02-10 | 1996-10-15 | Schering Ag | Pharmaceutical preparations for tnf inhibition |
| DE19540475A1 (de) * | 1995-10-20 | 1997-04-24 | Schering Ag | Chirale Methylphenyloxazolidinone |
| NZ322197A (en) * | 1995-11-21 | 1999-02-25 | Yamanouchi Pharma Co Ltd | Pyrido[2,3-d] pyrimidine derivatives and pharmaceutical compositions thereof |
| JP2000119272A (ja) | 1998-10-15 | 2000-04-25 | Nippon Zoki Pharmaceut Co Ltd | 新規７−アミノピリド〔２，３−ｄ〕ピリミジン誘導体 |
| US6455554B1 (en) | 1999-06-07 | 2002-09-24 | Targacept, Inc. | Oxopyridinyl pharmaceutical compositions and methods for use |
| EP1671651B1 (en) | 1999-08-21 | 2009-11-11 | Nycomed GmbH | Synergistic combination of pumafentrine and salmeterol |
| TWI243055B (en) | 2000-04-13 | 2005-11-11 | Nippon Zoki Pharmaceutical Co | Pharmaceutical composition for use in treatment of dermatitis |
| US6825180B2 (en) | 2001-05-18 | 2004-11-30 | Cell Therapeutics, Inc. | Pyridopyrimidine compounds and their uses |
| MXPA04004177A (es) * | 2001-11-01 | 2004-09-06 | Janssen Pharmaceutica Nv | Derivados de amida como inhibidores de la glicogeno cintasa cinasa 3-beta. |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006522151A (ja) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
| WO2006019965A2 (en) * | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| TW200726767A (en) * | 2005-07-04 | 2007-07-16 | Astrazeneca Ab | Chemical compounds 2 |
| TW200800997A (en) * | 2006-03-22 | 2008-01-01 | Astrazeneca Ab | Chemical compounds |
| CN101573358B (zh) * | 2006-09-15 | 2012-05-30 | 辉瑞产品公司 | 吡啶并(2,3-d)嘧啶酮化合物及其作为pi3抑制剂的用途 |
| SA08280783B1 (ar) * | 2007-01-11 | 2011-04-24 | استرازينيكا ايه بي | مشتقات بيريدوبيريميدين كمثبطات pde4 |
| WO2008084236A1 (en) * | 2007-01-11 | 2008-07-17 | Astrazeneca Ab | Chemical compounds 635 : pyridopyrimidinediones as pde4 inhibitors |
| TW200835497A (en) * | 2007-01-11 | 2008-09-01 | Astrazeneca Ab | Chemical compounds 636 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| AU2008261102B2 (en) | 2007-06-04 | 2013-11-28 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| FR2921926B1 (fr) * | 2007-10-03 | 2009-12-04 | Sanofi Aventis | Derives de quinazolinedione,leur preparation et leurs applications therapeutiques. |
| JP5607032B2 (ja) | 2008-05-27 | 2014-10-15 | アストラゼネカ・アクチエボラーグ | フェノキシピリジニルアミド誘導体およびｐｄｅ４仲介疾患状態におけるその使用 |
| CA2930674A1 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP3241839B1 (en) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| FR2944282B1 (fr) | 2009-04-09 | 2013-05-03 | Sanofi Aventis | Derives de quinazolinedione, leur preparation et leurs diverses applications therapeutiques |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EA201391254A1 (ru) | 2011-03-01 | 2014-02-28 | Синерджи Фармасьютикалз Инк. | Способ получения агонистов гуанилатциклазы c |
| US9545446B2 (en) | 2013-02-25 | 2017-01-17 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| HK1220611A1 (zh) | 2013-03-15 | 2017-05-12 | Bausch Health Ireland Limited | 用於治疗胃肠道病症的组成物 |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| SI3004138T1 (sl) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Limited | Ultra čisti agonisti gvanilat ciklaze C, postopek za njihovo pripravo in uporabo |
| US20160184387A1 (en) | 2013-08-09 | 2016-06-30 | Dominique Charmot | Compounds and methods for inhibiting phosphate transport |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
| WO2023042879A1 (ja) * | 2021-09-17 | 2023-03-23 | 塩野義製薬株式会社 | ウイルス増殖阻害活性を有する二環性複素環誘導体およびそれらを含有する医薬組成物 |
| CN113831491B (zh) * | 2021-09-30 | 2023-03-24 | 南昌大学 | 一种嘧啶唑共价有机框架的制备方法及吸附应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5649917B2 (OSRAM) * | 1973-12-18 | 1981-11-25 | ||
| DE2523730A1 (de) * | 1974-06-12 | 1976-02-12 | Hisamitsu Pharmaceutical Co | Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidinonen |
| JPS58428B2 (ja) * | 1974-07-05 | 1983-01-06 | ヒサミツセイヤク カブシキガイシヤ | シンキナ ２− オキソ −１，２，３，４− テトラヒドロピリド （ ２，３−ｄ ） ピリミジンユウドウタイノ セイゾウホウ |
| DE3770095D1 (de) * | 1986-08-21 | 1991-06-20 | Pfizer | Chinazolindione und pyridopyrimidindione. |
| JPH07506369A (ja) * | 1992-04-29 | 1995-07-13 | エス・アール・アイ・インターナシヨナル | 炎症を処置するためのデアザアミノプテリン |
-
1992
- 1992-03-20 US US07/855,179 patent/US5264437A/en not_active Expired - Lifetime
-
1993
- 1993-03-18 TW TW082101993A patent/TW240226B/zh active
- 1993-03-18 MX MX9301530A patent/MX9301530A/es not_active IP Right Cessation
- 1993-03-18 KR KR1019940703294A patent/KR100274104B1/ko not_active Expired - Fee Related
- 1993-03-18 HU HU9402653A patent/HUT67552A/hu unknown
- 1993-03-18 CN CN93103352A patent/CN1040327C/zh not_active Expired - Fee Related
- 1993-03-18 EP EP93908322A patent/EP0631580A1/en not_active Ceased
- 1993-03-18 NZ NZ251525A patent/NZ251525A/en unknown
- 1993-03-18 ZA ZA931945A patent/ZA931945B/xx unknown
- 1993-03-18 WO PCT/US1993/002273 patent/WO1993019068A1/en not_active Ceased
- 1993-03-18 JP JP51663493A patent/JP3241384B2/ja not_active Expired - Fee Related
- 1993-03-18 AU AU39186/93A patent/AU669520B2/en not_active Ceased
- 1993-03-18 IL IL105092A patent/IL105092A/en not_active IP Right Cessation
- 1993-03-18 CA CA002132297A patent/CA2132297C/en not_active Expired - Fee Related
- 1993-03-18 EP EP05023665A patent/EP1770093A1/en not_active Withdrawn
-
1994
- 1994-09-16 FI FI944305A patent/FI106960B/fi not_active IP Right Cessation
- 1994-09-16 NO NO943456A patent/NO301763B1/no not_active IP Right Cessation
-
1995
- 1995-04-24 HU HU95P/P00114P patent/HU210873A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL105092A (en) | 1998-06-15 |
| JPH07504676A (ja) | 1995-05-25 |
| MX9301530A (es) | 1994-01-31 |
| CA2132297C (en) | 2006-01-03 |
| AU3918693A (en) | 1993-10-21 |
| CA2132297A1 (en) | 1993-09-30 |
| FI944305L (fi) | 1994-09-16 |
| HU9402653D0 (en) | 1994-11-28 |
| CN1040327C (zh) | 1998-10-21 |
| IL105092A0 (en) | 1993-07-08 |
| FI944305A0 (fi) | 1994-09-16 |
| EP1770093A1 (en) | 2007-04-04 |
| HUT67552A (en) | 1995-04-28 |
| NO943456L (no) | 1994-09-16 |
| HU210873A9 (en) | 1995-08-28 |
| WO1993019068A1 (en) | 1993-09-30 |
| US5264437A (en) | 1993-11-23 |
| EP0631580A1 (en) | 1995-01-04 |
| KR100274104B1 (ko) | 2000-12-15 |
| NO301763B1 (no) | 1997-12-08 |
| TW240226B (OSRAM) | 1995-02-11 |
| KR950700909A (ko) | 1995-02-20 |
| JP3241384B2 (ja) | 2001-12-25 |
| NO943456D0 (no) | 1994-09-16 |
| ZA931945B (en) | 1994-09-18 |
| NZ251525A (en) | 1996-09-25 |
| CN1078470A (zh) | 1993-11-17 |
| AU669520B2 (en) | 1996-06-13 |
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