DD201896A5 - Verfahren zur herstellung neuer in 5-position substituierter 2,4-diamino-pyrimidine - Google Patents
Verfahren zur herstellung neuer in 5-position substituierter 2,4-diamino-pyrimidine Download PDFInfo
- Publication number
- DD201896A5 DD201896A5 DD81234745A DD23474581A DD201896A5 DD 201896 A5 DD201896 A5 DD 201896A5 DD 81234745 A DD81234745 A DD 81234745A DD 23474581 A DD23474581 A DD 23474581A DD 201896 A5 DD201896 A5 DD 201896A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- diamino
- pyrimidine
- radical
- amino
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 77
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 18
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 125000002252 acyl group Chemical group 0.000 claims abstract description 19
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- -1 cyano, hydroxy, mercapto Chemical class 0.000 claims description 156
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 49
- 150000003254 radicals Chemical class 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 20
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- NWFFAMNYFYKTDZ-UHFFFAOYSA-N 5-[(7,8-dimethoxy-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CCOC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N NWFFAMNYFYKTDZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 10
- MMDZZHAZMNJFMW-UHFFFAOYSA-N (2,4-diaminopyrimidin-5-yl)methanol Chemical compound NC1=NC=C(CO)C(N)=N1 MMDZZHAZMNJFMW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
- DCTFGGVNZYFNGJ-UHFFFAOYSA-N 5-[(2,4-diaminopyrimidin-5-yl)methyl]-7-methoxyquinolin-8-ol Chemical compound C=12C=CC=NC2=C(O)C(OC)=CC=1CC1=CN=C(N)N=C1N DCTFGGVNZYFNGJ-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- OQZGLXOADHKTDN-UHFFFAOYSA-N 1-oxidopyrimidin-1-ium Chemical compound [O-][N+]1=CC=CN=C1 OQZGLXOADHKTDN-UHFFFAOYSA-N 0.000 claims description 3
- SNBAXPMOWGZMOL-UHFFFAOYSA-N 5-[(2,4-diaminopyrimidin-5-yl)methyl]-7,8-dimethoxychromen-2-one Chemical compound C=12C=CC(=O)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N SNBAXPMOWGZMOL-UHFFFAOYSA-N 0.000 claims description 3
- YXVYIKAJJZFIQN-UHFFFAOYSA-N 5-[(7,8-dimethoxy-2-methyl-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC(C)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N YXVYIKAJJZFIQN-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- GKQJABQIIZIFFZ-UHFFFAOYSA-N 5-[(4-amino-3-methoxynaphthalen-1-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=CC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N GKQJABQIIZIFFZ-UHFFFAOYSA-N 0.000 claims description 2
- ZCONNBVJQVEVEB-UHFFFAOYSA-N 5-[(7-methoxy-8-nitroquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C([N+]([O-])=O)C(OC)=CC=1CC1=CN=C(N)N=C1N ZCONNBVJQVEVEB-UHFFFAOYSA-N 0.000 claims description 2
- GVNXJSKJOJYPOC-UHFFFAOYSA-N 5-[(8-amino-7-methoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N GVNXJSKJOJYPOC-UHFFFAOYSA-N 0.000 claims description 2
- GEZCGCFDXURYSM-UHFFFAOYSA-N 5-[(8-amino-7-methylsulfanylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(SC)=CC=1CC1=CN=C(N)N=C1N GEZCGCFDXURYSM-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- AIOWJIMWVFWROP-UHFFFAOYSA-N baquiloprim Chemical compound C12=CC=CN=C2C(N(C)C)=C(C)C=C1CC1=CN=C(N)N=C1N AIOWJIMWVFWROP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000007068 beta-elimination reaction Methods 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- URPGJMLVVSCAKX-UHFFFAOYSA-N 5-[(7,8-dimethoxy-2-methyl-4h-chromen-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12CC=C(C)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N URPGJMLVVSCAKX-UHFFFAOYSA-N 0.000 claims 1
- OQFGIDFOQYUQAF-UHFFFAOYSA-N 5-[(7,8-dimethoxy-3,4-dihydro-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12CCCOC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N OQFGIDFOQYUQAF-UHFFFAOYSA-N 0.000 claims 1
- UEZUWFLRLFLRDB-UHFFFAOYSA-N 5-[(7,8-dimethoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N UEZUWFLRLFLRDB-UHFFFAOYSA-N 0.000 claims 1
- DDYFWXNCUMRKPM-UHFFFAOYSA-N 5-[(7-methylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=CC(C)=CC=1CC1=CN=C(N)N=C1N DDYFWXNCUMRKPM-UHFFFAOYSA-N 0.000 claims 1
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 238000001275 scanning Auger electron spectroscopy Methods 0.000 claims 1
- 101150068774 thyX gene Proteins 0.000 claims 1
- 125000005490 tosylate group Chemical class 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 abstract description 10
- 150000003456 sulfonamides Chemical class 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 230000009044 synergistic interaction Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 211
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
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- 229960005404 sulfamethoxazole Drugs 0.000 description 17
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 17
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- 238000005481 NMR spectroscopy Methods 0.000 description 13
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- 229940125904 compound 1 Drugs 0.000 description 13
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 10
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- 239000000706 filtrate Substances 0.000 description 9
- 229960004198 guanidine Drugs 0.000 description 9
- DRGCXLJWMQGVJA-UHFFFAOYSA-N pyrimidine;dihydrochloride Chemical compound Cl.Cl.C1=CN=CN=C1 DRGCXLJWMQGVJA-UHFFFAOYSA-N 0.000 description 9
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- 241000283690 Bos taurus Species 0.000 description 8
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8036135 | 1980-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201896A5 true DD201896A5 (de) | 1983-08-17 |
Family
ID=10517217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81234745A DD201896A5 (de) | 1980-11-11 | 1981-11-10 | Verfahren zur herstellung neuer in 5-position substituierter 2,4-diamino-pyrimidine |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US4438267A (cs) |
| EP (1) | EP0051879B1 (cs) |
| JP (1) | JPS57114581A (cs) |
| KR (1) | KR880001736B1 (cs) |
| AR (1) | AR245447A1 (cs) |
| AU (1) | AU549449B2 (cs) |
| CA (1) | CA1186310A (cs) |
| CS (1) | CS273153B2 (cs) |
| CY (1) | CY1419A (cs) |
| DD (1) | DD201896A5 (cs) |
| DE (1) | DE3173752D1 (cs) |
| DK (1) | DK172884B1 (cs) |
| EG (1) | EG16107A (cs) |
| ES (5) | ES506969A0 (cs) |
| FI (1) | FI76333C (cs) |
| GB (1) | GB2087881B (cs) |
| GR (1) | GR81317B (cs) |
| HK (1) | HK23388A (cs) |
| HU (1) | HU188762B (cs) |
| IE (1) | IE52128B1 (cs) |
| IL (1) | IL64256A (cs) |
| IT (1) | IT1210589B (cs) |
| MC (1) | MC1418A1 (cs) |
| MY (1) | MY8600678A (cs) |
| NO (2) | NO160137C (cs) |
| NZ (1) | NZ198932A (cs) |
| PH (2) | PH25053A (cs) |
| PL (4) | PL139427B1 (cs) |
| PT (1) | PT73960B (cs) |
| RU (1) | RU1819264C (cs) |
| SG (1) | SG62686G (cs) |
| SU (4) | SU1424732A3 (cs) |
| YU (5) | YU42444B (cs) |
| ZA (1) | ZA817780B (cs) |
| ZM (1) | ZM9481A1 (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
| US4590271A (en) * | 1982-05-01 | 1986-05-20 | Burroughs Wellcome Co. | 2,4-diamino-5-(substituted)pyrimidines, useful as antimicrobials |
| ZA833067B (en) * | 1982-05-01 | 1984-12-24 | Wellcome Found | Antibacterial compounds |
| DK190983A (da) * | 1982-05-01 | 1983-11-02 | Wellcome Found | 2,4-diamino-5-(substituerede)pyrimidiner, fremgangsmaade til deres fremstilling og mellemprodukter derfor |
| US4587341A (en) * | 1982-05-07 | 1986-05-06 | Burroughs Wellcome Co. | 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials |
| CA1244028A (en) * | 1983-04-14 | 1988-11-01 | Hans Maag | Pyrimidine derivatives |
| GB8603964D0 (en) * | 1986-02-18 | 1986-03-26 | Cooper Animal Health Ltd | Compositions |
| GB8603962D0 (en) * | 1986-02-18 | 1986-03-26 | Wellcome Found | Chemical compositions |
| LU86703A1 (fr) * | 1986-12-08 | 1988-07-14 | Oreal | Composition cosmetique photostable contenant un filtre uv-a et un filtre uv-b,son utilisation pour la protection de la peau contre les rayons uv et procede de stabilisation du filtre uv-a par le filtre uv-b |
| FI895821A7 (fi) * | 1988-12-07 | 1990-06-08 | The Wellcome Foundation Ltd | Farmaseuttisesti aktivisia CNS-yhdisteitä |
| GB8903978D0 (en) * | 1989-02-22 | 1989-04-05 | Coopers Animal Health | Chemical compositions |
| GB9000241D0 (en) * | 1990-01-05 | 1990-03-07 | Coopers Animal Health | Pharmaceutical use |
| RU95113597A (ru) * | 1992-12-02 | 1997-06-10 | ФМК Корпорейшн (US) | Инсектицидная композиция, способы борьбы с насекомыми |
| NO940245D0 (no) * | 1993-01-28 | 1994-01-24 | Takeda Chemical Industries Ltd | Quinolin eller quinazolinderivater, deres fremstilling og anvendelse |
| US5707996A (en) * | 1995-11-06 | 1998-01-13 | Macleod Pharmaceuticals, Inc. | Pharmaceutical solution and methods for preparation thereof |
| CA2238521C (en) * | 1995-12-04 | 2005-08-16 | F. Hoffmann-La Roche Ag | Diaminopyrimidines, pharmaceutical compositions containing them and their use as antibacterial |
| RU2141322C1 (ru) * | 1997-08-12 | 1999-11-20 | Голощапов Николай Михайлович | Иммуномодулятор с антимикобактериальной активностью "изофон", способ его получения и применения |
| GB0016877D0 (en) * | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| DE60216281T2 (de) * | 2001-06-29 | 2007-07-05 | Ab Science | Die verwendung von tyrosinkinasehemmer zur behandlung von allergischen erkrankungen |
| CA2452169A1 (en) * | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating inflammatory diseases |
| DK1401416T5 (da) | 2001-06-29 | 2007-03-19 | Ab Science | Anvendelse af C-kit-inhibitorer til behandling af inflammatorisk tarmsygdom |
| ATE376182T1 (de) * | 2001-06-29 | 2007-11-15 | Ab Science | C-kit inhibitoren |
| US20040242612A1 (en) * | 2001-09-20 | 2004-12-02 | Alain Moussy | Use of tyrosine kinase inhibitors for promoting hair growth |
| DE60228278D1 (de) * | 2001-09-20 | 2008-09-25 | Ab Science | Die verwendung von potenten, selektiven und nontoxischen c-kithemmern zur behandlung von interstitieller blasenentzündung |
| WO2003035049A2 (en) * | 2001-09-20 | 2003-05-01 | Ab Science | Use of potent, selective and non-toxic c-kit inhibitors for treating bacterial infections |
| ATE469146T1 (de) * | 2003-07-11 | 2010-06-15 | Arpida Ag | Benzofuranderivate und deren verwendung bei der behandlung von mikrobiellen infektionen |
| NZ556800A (en) * | 2005-02-18 | 2011-01-28 | Acino Pharma Ag | Novel processes for the preparation of a 2H-chromene (Iclaprim) |
| MX2008002731A (es) * | 2005-09-01 | 2008-03-26 | Hoffmann La Roche | Diaminopirimidinas como moduladores de p2x3 y p3x2/3. |
| US20100029689A1 (en) * | 2008-07-02 | 2010-02-04 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| JP5756096B2 (ja) * | 2009-06-12 | 2015-07-29 | ソックプラ−シアンセ エ ジェニー エス．ウ．セ． | グアニンリボスイッチ結合化合物及び抗生物質としてのその使用 |
| CN102649786B (zh) * | 2011-02-28 | 2014-08-27 | 郑州福源动物药业有限公司 | 一种2，4-二氨基-5-(8-二甲氨基-7-甲基-5-喹啉基甲基)-2，4-(1h，3h)嘧啶的制备方法 |
| CN103755684B (zh) * | 2014-02-10 | 2015-09-09 | 青岛蔚蓝生物股份有限公司 | 一种巴喹普林的制备方法 |
| CN113924293B (zh) * | 2019-06-06 | 2024-07-09 | 北京泰德制药股份有限公司 | P2x3和/或p2x2/3受体拮抗剂、包含其的药物组合物及其用途 |
| CN110818694B (zh) * | 2019-11-18 | 2023-04-21 | 上海医药工业研究院有限公司 | 艾拉普林中间体及其应用 |
| US20240226100A1 (en) * | 2021-04-09 | 2024-07-11 | The Trustees Of The University Of Pennsylvania | Control of protein expression with tmp-protac compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049544A (en) * | 1962-08-14 | Method for the preparation of | ||
| DE1303727B (de) | 1959-09-03 | 1976-02-05 | Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London | Alpha-Arylidensubstituierte Propioni-Irile |
| US3956327A (en) * | 1969-03-06 | 1976-05-11 | Burroughs Wellcome Co. | Method of preparing 2,4-diamino-5-benzyl pyrimidines |
| BE792096A (fr) * | 1971-12-01 | 1973-05-30 | Hoffmann La Roche | Nouvelles benzylpyrimidines |
| GB1468374A (en) | 1974-03-06 | 1977-03-23 | Wellcome Found | Process for preparing a pyrimidine derivative |
| US4039543A (en) | 1974-12-24 | 1977-08-02 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| GB1582245A (en) * | 1976-06-09 | 1981-01-07 | Wellcome Found | Benzyl cyanoacetal derivatives and their conversion to pyrimidine derivatives |
| DE2730467A1 (de) * | 1977-07-06 | 1979-01-18 | Basf Ag | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4258045A (en) * | 1979-11-30 | 1981-03-24 | Merck & Co., Inc. | Inhibitor of dihydrofolate reductase |
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
-
1981
- 1981-11-09 US US06/319,644 patent/US4438267A/en not_active Expired - Lifetime
- 1981-11-10 PL PL1981239279A patent/PL139427B1/pl unknown
- 1981-11-10 CA CA000389807A patent/CA1186310A/en not_active Expired
- 1981-11-10 DK DK198104966A patent/DK172884B1/da active Protection Beyond IP Right Term
- 1981-11-10 IE IE2631/81A patent/IE52128B1/en not_active IP Right Cessation
- 1981-11-10 PL PL1981239278A patent/PL139827B1/pl unknown
- 1981-11-10 SU SU813358051A patent/SU1424732A3/ru active
- 1981-11-10 NO NO813804A patent/NO160137C/no not_active IP Right Cessation
- 1981-11-10 FI FI813546A patent/FI76333C/fi not_active IP Right Cessation
- 1981-11-10 NZ NZ198932A patent/NZ198932A/en unknown
- 1981-11-10 IL IL64256A patent/IL64256A/xx not_active IP Right Cessation
- 1981-11-10 PL PL1981233754A patent/PL139523B1/pl unknown
- 1981-11-10 ZA ZA817780A patent/ZA817780B/xx unknown
- 1981-11-10 KR KR1019810004348A patent/KR880001736B1/ko not_active Expired
- 1981-11-10 EG EG653/81A patent/EG16107A/xx active
- 1981-11-10 CS CS825781A patent/CS273153B2/cs unknown
- 1981-11-10 GR GR66482A patent/GR81317B/el unknown
- 1981-11-10 IT IT8149676A patent/IT1210589B/it active
- 1981-11-10 ES ES506969A patent/ES506969A0/es active Granted
- 1981-11-10 MC MC811560A patent/MC1418A1/xx unknown
- 1981-11-10 AU AU77334/81A patent/AU549449B2/en not_active Expired
- 1981-11-10 HU HU813359A patent/HU188762B/hu unknown
- 1981-11-10 YU YU2663/81A patent/YU42444B/xx unknown
- 1981-11-10 PT PT73960A patent/PT73960B/pt unknown
- 1981-11-10 PL PL1981239280A patent/PL139828B1/pl unknown
- 1981-11-10 DD DD81234745A patent/DD201896A5/de not_active IP Right Cessation
- 1981-11-10 GB GB8133833A patent/GB2087881B/en not_active Expired
- 1981-11-10 JP JP56180271A patent/JPS57114581A/ja active Granted
- 1981-11-11 ZM ZM94/81A patent/ZM9481A1/xx unknown
- 1981-11-11 EP EP81109631A patent/EP0051879B1/en not_active Expired
- 1981-11-11 DE DE8181109631T patent/DE3173752D1/de not_active Expired
- 1981-11-11 CY CY141981A patent/CY1419A/xx unknown
-
1983
- 1983-01-27 SU SU833543245A patent/SU1318148A3/ru active
- 1983-01-31 SU SU833547444A patent/SU1306473A3/ru active
- 1983-04-02 ES ES521201A patent/ES521201A0/es active Granted
- 1983-04-02 ES ES521203A patent/ES8405379A1/es not_active Expired
- 1983-04-02 ES ES521202A patent/ES521202A0/es active Granted
- 1983-04-02 ES ES521204A patent/ES521204A0/es active Granted
- 1983-09-07 PH PH29503A patent/PH25053A/en unknown
- 1983-09-07 PH PH29502A patent/PH22654A/en unknown
- 1983-10-03 YU YU01982/83A patent/YU198283A/xx unknown
- 1983-10-03 YU YU1983/83A patent/YU43551B/xx unknown
- 1983-10-03 YU YU01981/83A patent/YU198183A/xx unknown
- 1983-10-31 US US06/546,850 patent/US4587342A/en not_active Expired - Lifetime
- 1983-12-30 US US06/567,248 patent/US4603136A/en not_active Expired - Lifetime
-
1986
- 1986-02-02 RU SU863552053A patent/RU1819264C/ru active
- 1986-03-12 US US06/839,463 patent/US4761475A/en not_active Expired - Lifetime
- 1986-07-17 SG SG626/86A patent/SG62686G/en unknown
- 1986-12-30 MY MY678/86A patent/MY8600678A/xx unknown
-
1987
- 1987-01-14 SU SU874028793A patent/SU1535379A3/ru active
-
1988
- 1988-03-30 HK HK233/88A patent/HK23388A/en not_active IP Right Cessation
- 1988-06-17 AR AR88311165A patent/AR245447A1/es active
- 1988-07-26 YU YU144288A patent/YU46697B/sh unknown
-
1994
- 1994-12-29 NO NO1994029C patent/NO1994029I1/no unknown
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| ENJ | Ceased due to non-payment of renewal fee |