NO843003L - Fremgangsmaate for fremstilling av terapeutisk aktive triazolo-pyrimidin-derivater - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive triazolo-pyrimidin-derivaterInfo
- Publication number
- NO843003L NO843003L NO843003A NO843003A NO843003L NO 843003 L NO843003 L NO 843003L NO 843003 A NO843003 A NO 843003A NO 843003 A NO843003 A NO 843003A NO 843003 L NO843003 L NO 843003L
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- triazolo
- pyrimidine
- oxo
- methyl
- Prior art date
Links
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 15
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 230000003177 cardiotonic effect Effects 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 29
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000004936 stimulating effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GSUNBHMXVORMRQ-UHFFFAOYSA-N 2-hydrazinyl-6-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound O=C1NC(NN)=NC(C=2N=CC=CC=2)=C1 GSUNBHMXVORMRQ-UHFFFAOYSA-N 0.000 description 2
- OXWAZGBAKXJRTN-UHFFFAOYSA-N 2-hydrazinyl-6-pyridin-3-yl-1h-pyrimidin-4-one Chemical compound O=C1NC(NN)=NC(C=2C=NC=CC=2)=C1 OXWAZGBAKXJRTN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 melting point 250°C Chemical compound 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000009090 positive inotropic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- QPCHNVHKEGKAIH-UHFFFAOYSA-N 2-hydrazinyl-5-pyridin-3-yl-1h-pyrimidin-6-one Chemical compound O=C1NC(NN)=NC=C1C1=CC=CN=C1 QPCHNVHKEGKAIH-UHFFFAOYSA-N 0.000 description 1
- FRBWYXDJEDXREB-UHFFFAOYSA-N 2-hydrazinyl-6-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound O=C1NC(NN)=NC(C=2C=CN=CC=2)=C1 FRBWYXDJEDXREB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010007556 Cardiac failure acute Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 229940011411 erythrosine Drugs 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8312443A FR2549834B1 (fr) | 1983-07-25 | 1983-07-25 | Derives de triazolo-pyrimidine, leur procede de preparation et leur application therapeutique en tant que tonicardiaques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO843003L true NO843003L (no) | 1985-01-28 |
Family
ID=9291173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO843003A NO843003L (no) | 1983-07-25 | 1984-07-24 | Fremgangsmaate for fremstilling av terapeutisk aktive triazolo-pyrimidin-derivater |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4581358A (ko) |
| EP (1) | EP0136198B1 (ko) |
| JP (1) | JPS6051190A (ko) |
| KR (1) | KR870001200B1 (ko) |
| AT (1) | ATE32462T1 (ko) |
| AU (1) | AU562596B2 (ko) |
| CA (1) | CA1226284A (ko) |
| CS (1) | CS248718B2 (ko) |
| DD (1) | DD222593A5 (ko) |
| DE (1) | DE3469300D1 (ko) |
| DK (1) | DK360584A (ko) |
| ES (1) | ES8504806A1 (ko) |
| FI (1) | FI842966A (ko) |
| FR (1) | FR2549834B1 (ko) |
| GR (1) | GR82222B (ko) |
| HU (1) | HU190653B (ko) |
| IL (1) | IL72330A (ko) |
| MA (1) | MA20186A1 (ko) |
| NO (1) | NO843003L (ko) |
| NZ (1) | NZ208991A (ko) |
| OA (1) | OA07755A (ko) |
| PH (1) | PH20003A (ko) |
| PL (1) | PL248923A1 (ko) |
| PT (1) | PT78970B (ko) |
| SU (1) | SU1347865A3 (ko) |
| YU (1) | YU131784A (ko) |
| ZA (1) | ZA845301B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666908A (en) * | 1985-04-05 | 1987-05-19 | Warner-Lambert Company | 5-Substituted pyrazolo[4,3-d]pyrimidine-7-ones and methods of use |
| US4883872A (en) * | 1987-11-25 | 1989-11-28 | E. R. Squibb & Sons, Inc. | 3-oxo-1,2,4-triazolo(4,3-A) pyrimidine-6-carboxylic acid esters |
| US4892945A (en) * | 1987-12-21 | 1990-01-09 | Ciba-Geigy Corporation | Isoindoline pigments containing at least one triazolopyrimidone radical |
| KR100324966B1 (ko) * | 1999-04-13 | 2002-02-25 | 서정윤 | 알루미늄제품의 전해착색법 |
| JP7332472B2 (ja) * | 2016-12-22 | 2023-08-23 | ノバルティス アーゲー | Ｎｍｄａ受容体モジュレーターおよびその使用 |
| CN112513047B (zh) | 2018-08-03 | 2023-10-20 | 诺华股份有限公司 | 芳香杂环nmda受体调节剂及其用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB845552A (en) * | 1955-10-26 | 1960-08-24 | Farmaceutici Italia | Pyrimidine derivatives |
| US4209621A (en) * | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
-
1983
- 1983-07-25 FR FR8312443A patent/FR2549834B1/fr not_active Expired
-
1984
- 1984-07-06 IL IL72330A patent/IL72330A/xx unknown
- 1984-07-09 US US06/628,916 patent/US4581358A/en not_active Expired - Fee Related
- 1984-07-10 ZA ZA845301A patent/ZA845301B/xx unknown
- 1984-07-18 AU AU30791/84A patent/AU562596B2/en not_active Ceased
- 1984-07-20 KR KR1019840004279A patent/KR870001200B1/ko not_active IP Right Cessation
- 1984-07-23 DK DK360584A patent/DK360584A/da not_active Application Discontinuation
- 1984-07-23 CS CS845626A patent/CS248718B2/cs unknown
- 1984-07-23 MA MA20410A patent/MA20186A1/fr unknown
- 1984-07-23 ES ES534550A patent/ES8504806A1/es not_active Expired
- 1984-07-24 CA CA000459573A patent/CA1226284A/fr not_active Expired
- 1984-07-24 PT PT78970A patent/PT78970B/pt unknown
- 1984-07-24 PH PH31020A patent/PH20003A/en unknown
- 1984-07-24 EP EP84401551A patent/EP0136198B1/fr not_active Expired
- 1984-07-24 AT AT84401551T patent/ATE32462T1/de not_active IP Right Cessation
- 1984-07-24 DE DE8484401551T patent/DE3469300D1/de not_active Expired
- 1984-07-24 GR GR75412A patent/GR82222B/el unknown
- 1984-07-24 NZ NZ208991A patent/NZ208991A/en unknown
- 1984-07-24 NO NO843003A patent/NO843003L/no unknown
- 1984-07-25 JP JP59155127A patent/JPS6051190A/ja active Pending
- 1984-07-25 SU SU843767330A patent/SU1347865A3/ru active
- 1984-07-25 YU YU01317/84A patent/YU131784A/xx unknown
- 1984-07-25 PL PL24892384A patent/PL248923A1/xx unknown
- 1984-07-25 DD DD84265646A patent/DD222593A5/de unknown
- 1984-07-25 FI FI842966A patent/FI842966A/fi not_active Application Discontinuation
- 1984-07-25 OA OA58349A patent/OA07755A/xx unknown
- 1984-07-25 HU HU842861A patent/HU190653B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT34753A (en) | 1985-04-28 |
| EP0136198B1 (fr) | 1988-02-10 |
| AU562596B2 (en) | 1987-06-11 |
| OA07755A (fr) | 1985-08-30 |
| US4581358A (en) | 1986-04-08 |
| KR850001214A (ko) | 1985-03-16 |
| DE3469300D1 (en) | 1988-03-17 |
| MA20186A1 (fr) | 1985-04-01 |
| YU131784A (en) | 1986-06-30 |
| HU190653B (en) | 1986-10-28 |
| CA1226284A (fr) | 1987-09-01 |
| ES534550A0 (es) | 1985-05-01 |
| AU3079184A (en) | 1985-01-31 |
| FR2549834A1 (fr) | 1985-02-01 |
| DK360584A (da) | 1985-01-26 |
| PL248923A1 (en) | 1985-05-07 |
| FI842966A0 (fi) | 1984-07-25 |
| CS248718B2 (en) | 1987-02-12 |
| FI842966A (fi) | 1985-01-26 |
| FR2549834B1 (fr) | 1985-10-18 |
| ES8504806A1 (es) | 1985-05-01 |
| IL72330A (en) | 1987-02-27 |
| GR82222B (ko) | 1984-12-13 |
| NZ208991A (en) | 1987-07-31 |
| ZA845301B (en) | 1985-02-27 |
| IL72330A0 (en) | 1984-11-30 |
| ATE32462T1 (de) | 1988-02-15 |
| DK360584D0 (da) | 1984-07-23 |
| DD222593A5 (de) | 1985-05-22 |
| SU1347865A3 (ru) | 1987-10-23 |
| JPS6051190A (ja) | 1985-03-22 |
| PH20003A (en) | 1986-08-28 |
| PT78970A (fr) | 1984-08-01 |
| KR870001200B1 (ko) | 1987-06-20 |
| PT78970B (fr) | 1986-06-05 |
| EP0136198A1 (fr) | 1985-04-03 |
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