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)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Rheumatology (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 |
|---|---|---|---|
| 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 |
| US85517992 | 1992-03-20 | ||
| US9302273 | 1993-03-18 | ||
| PCT/US1993/002273 WO1993019068A1 (en) | 1992-03-20 | 1993-03-18 | PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS |
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 (ca) |
| EP (2) | EP0631580A1 (ca) |
| JP (1) | JP3241384B2 (ca) |
| KR (1) | KR100274104B1 (ca) |
| CN (1) | CN1040327C (ca) |
| AU (1) | AU669520B2 (ca) |
| CA (1) | CA2132297C (ca) |
| FI (1) | FI106960B (ca) |
| HU (2) | HUT67552A (ca) |
| IL (1) | IL105092A (ca) |
| MX (1) | MX9301530A (ca) |
| NO (1) | NO301763B1 (ca) |
| NZ (1) | NZ251525A (ca) |
| TW (1) | TW240226B (ca) |
| WO (1) | WO1993019068A1 (ca) |
| ZA (1) | ZA931945B (ca) |
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 |
| CA2197984A1 (en) * | 1994-08-29 | 1996-03-07 | Kazuhisa Takayama | Novel naphthyridine derivatives and pharmaceutical compositions thereof |
| HUP9702408A3 (en) * | 1995-02-10 | 2000-08-28 | Schering Ag | Use of 5-phenyloxazolidin-2-one derivatives for the preparation of pharmaceutical compositions treating diseases requiring tumour necrosis factor (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 |
| SK287231B6 (sk) | 1999-08-21 | 2010-04-07 | Nycomed Gmbh | Liečivo zahŕňajúce PDE inhibítor a agonistu beta2 adrenoreceptora |
| 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 |
| JP2005507419A (ja) | 2001-11-01 | 2005-03-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | グリコーゲン合成酵素キナーゼ３ベータ阻害剤としてのアミド誘導体 |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| AU2004226353A1 (en) | 2003-04-01 | 2004-10-14 | Laboratoires Serono Sa | Inhibitors of phosphodiesterases in infertility |
| 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 |
| GEP20115306B (ca) * | 2006-09-15 | 2011-10-10 | Pfizer Prod Inc | |
| 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 |
| SA08280783B1 (ar) * | 2007-01-11 | 2011-04-24 | استرازينيكا ايه بي | مشتقات بيريدوبيريميدين كمثبطات pde4 |
| 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 |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| 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 |
| FR2921926B1 (fr) * | 2007-10-03 | 2009-12-04 | Sanofi Aventis | Derives de quinazolinedione,leur preparation et leurs applications therapeutiques. |
| PL2297106T3 (pl) | 2008-05-27 | 2015-01-30 | Galderma Sa | Pochodne fenoksypirydynyloamidu i ich zastosowania w leczeniu chorób, w których pośredniczy pde4 |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| 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 |
| KR102034748B1 (ko) | 2011-03-01 | 2019-10-21 | 시너지 파마슈티컬즈 인코포레이티드 | 구아닐레이트 사이클라제 c 작용제의 제조 방법 |
| US9545446B2 (en) | 2013-02-25 | 2017-01-17 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | 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 |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| JP6694385B2 (ja) | 2013-08-09 | 2020-05-13 | アーデリクス，インコーポレーテッド | リン酸塩輸送阻害のための化合物及び方法 |
| CN114340631A (zh) | 2019-05-21 | 2022-04-12 | 阿德利克斯股份有限公司 | 用于降低患者的血清磷酸盐的组合 |
| JPWO2023042879A1 (ca) * | 2021-09-17 | 2023-03-23 | ||
| 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 (ca) * | 1973-12-18 | 1981-11-25 | ||
| 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 |
| DE2523730A1 (de) * | 1974-06-12 | 1976-02-12 | Hisamitsu Pharmaceutical Co | Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidinonen |
| DE3770095D1 (de) * | 1986-08-21 | 1991-06-20 | Pfizer | Chinazolindione und pyridopyrimidindione. |
| CA2133442A1 (en) * | 1992-04-29 | 1993-11-11 | James R. Piper | Deazaaminopterins for treatment of inflammation |
-
1992
- 1992-03-20 US US07/855,179 patent/US5264437A/en not_active Expired - Lifetime
-
1993
- 1993-03-18 EP EP93908322A patent/EP0631580A1/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 CN CN93103352A patent/CN1040327C/zh not_active Expired - Fee Related
- 1993-03-18 KR KR1019940703294A patent/KR100274104B1/ko not_active Expired - Fee Related
- 1993-03-18 JP JP51663493A patent/JP3241384B2/ja not_active Expired - Fee Related
- 1993-03-18 WO PCT/US1993/002273 patent/WO1993019068A1/en not_active Ceased
- 1993-03-18 HU HU9402653A patent/HUT67552A/hu unknown
- 1993-03-18 ZA ZA931945A patent/ZA931945B/xx unknown
- 1993-03-18 NZ NZ251525A patent/NZ251525A/en unknown
- 1993-03-18 EP EP05023665A patent/EP1770093A1/en not_active Withdrawn
- 1993-03-18 AU AU39186/93A patent/AU669520B2/en not_active Ceased
- 1993-03-18 MX MX9301530A patent/MX9301530A/es not_active IP Right Cessation
- 1993-03-18 TW TW082101993A patent/TW240226B/zh active
-
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 |
|---|---|
| NO301763B1 (no) | 1997-12-08 |
| NO943456L (no) | 1994-09-16 |
| NO943456D0 (no) | 1994-09-16 |
| JPH07504676A (ja) | 1995-05-25 |
| EP0631580A1 (en) | 1995-01-04 |
| JP3241384B2 (ja) | 2001-12-25 |
| HU9402653D0 (en) | 1994-11-28 |
| FI944305L (fi) | 1994-09-16 |
| US5264437A (en) | 1993-11-23 |
| CA2132297C (en) | 2006-01-03 |
| IL105092A (en) | 1998-06-15 |
| HU210873A9 (en) | 1995-08-28 |
| TW240226B (ca) | 1995-02-11 |
| CA2132297A1 (en) | 1993-09-30 |
| AU669520B2 (en) | 1996-06-13 |
| IL105092A0 (en) | 1993-07-08 |
| EP1770093A1 (en) | 2007-04-04 |
| FI944305A0 (fi) | 1994-09-16 |
| HUT67552A (en) | 1995-04-28 |
| KR950700909A (ko) | 1995-02-20 |
| CN1040327C (zh) | 1998-10-21 |
| NZ251525A (en) | 1996-09-25 |
| AU3918693A (en) | 1993-10-21 |
| MX9301530A (es) | 1994-01-31 |
| KR100274104B1 (ko) | 2000-12-15 |
| CN1078470A (zh) | 1993-11-17 |
| ZA931945B (en) | 1994-09-18 |
| WO1993019068A1 (en) | 1993-09-30 |
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