NO115741B - - Google Patents
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- Publication number
- NO115741B NO115741B NO160437A NO16043765A NO115741B NO 115741 B NO115741 B NO 115741B NO 160437 A NO160437 A NO 160437A NO 16043765 A NO16043765 A NO 16043765A NO 115741 B NO115741 B NO 115741B
- Authority
- NO
- Norway
- Prior art keywords
- water
- solution
- methanol
- formula
- sodium
- Prior art date
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- IAJBQAYHSQIQRE-UHFFFAOYSA-N 2,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C=C1OC IAJBQAYHSQIQRE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- DNAVOCNYHNNEQI-UHFFFAOYSA-N asaronaldehyde Natural products COC1=CC(OC)=C(C=CC=O)C=C1OC DNAVOCNYHNNEQI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- LXQRQVUSDOKVLD-UHFFFAOYSA-N 2,4,5-trichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=C(C=O)C=C1Cl LXQRQVUSDOKVLD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229960004198 guanidine Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960000654 sulfafurazole Drugs 0.000 description 2
- HZKGTRUEBFRMNO-UHFFFAOYSA-N (3,4,5-trichlorophenyl)methanol Chemical compound OCC1=CC(Cl)=C(Cl)C(Cl)=C1 HZKGTRUEBFRMNO-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 description 1
- GHMOHPITLLRUAC-UHFFFAOYSA-N 3,4,5-trichlorobenzaldehyde Chemical compound ClC1=CC(C=O)=CC(Cl)=C1Cl GHMOHPITLLRUAC-UHFFFAOYSA-N 0.000 description 1
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 description 1
- OXGJKCALURPRCN-UHFFFAOYSA-N 3-methoxypropanal Chemical compound COCCC=O OXGJKCALURPRCN-UHFFFAOYSA-N 0.000 description 1
- RMIZEUOAFVZZJG-UHFFFAOYSA-N 4,5-dimethoxy-2-methylbenzaldehyde Chemical compound COC1=CC(C)=C(C=O)C=C1OC RMIZEUOAFVZZJG-UHFFFAOYSA-N 0.000 description 1
- NHZLNPMOSADWGC-UHFFFAOYSA-N 4-amino-N-(2-quinoxalinyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 description 1
- FQLKASDBWGNDRZ-UHFFFAOYSA-N 5-[(2,4,5-trichlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC(Cl)=C(Cl)C=C1Cl FQLKASDBWGNDRZ-UHFFFAOYSA-N 0.000 description 1
- OCPCMYIYGAVFJT-UHFFFAOYSA-N 5-[(3,4,5-trichlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC(Cl)=C(Cl)C(Cl)=C1 OCPCMYIYGAVFJT-UHFFFAOYSA-N 0.000 description 1
- KEEYRKYKLYARHO-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1CC1=CN=C(N)N=C1N KEEYRKYKLYARHO-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000973 sulfadimethoxine Drugs 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- 229960003097 sulfaquinoxaline Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 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 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 1
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D239/30—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- 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
- 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
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41079364A | 1964-11-12 | 1964-11-12 | |
| US41071064A | 1964-11-12 | 1964-11-12 | |
| US45416865A | 1965-05-07 | 1965-05-07 | |
| US45417265A | 1965-05-07 | 1965-05-07 | |
| US46083465A | 1965-06-02 | 1965-06-02 | |
| US470917A US3341541A (en) | 1964-11-12 | 1965-07-09 | Processes and intermediates for pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115741B true NO115741B (it) | 1968-11-25 |
Family
ID=27559952
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160436A NO119948B (it) | 1964-11-12 | 1965-11-11 | |
| NO160437A NO115741B (it) | 1964-11-12 | 1965-11-11 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160436A NO119948B (it) | 1964-11-12 | 1965-11-11 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US3485840A (it) |
| BE (3) | BE671983A (it) |
| BR (3) | BR6574670D0 (it) |
| CH (2) | CH467784A (it) |
| DE (2) | DE1545966A1 (it) |
| DK (2) | DK125553B (it) |
| FI (1) | FI43251B (it) |
| FR (1) | FR5411M (it) |
| GB (7) | GB1132085A (it) |
| IL (7) | IL24497A (it) |
| IT (1) | IT1058251B (it) |
| MY (2) | MY6700159A (it) |
| NL (3) | NL6514178A (it) |
| NO (2) | NO119948B (it) |
| SE (4) | SE346314B (it) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485840A (en) * | 1964-11-12 | 1969-12-23 | Hoffmann La Roche | 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes |
| GB1142654A (en) * | 1965-10-28 | 1969-02-12 | Wellcome Found | Cyano-acetals and their use in benzylpyrimidine synthesis |
| US3515783A (en) * | 1967-10-20 | 1970-06-02 | Hoffmann La Roche | Antibacterial composition containing 5-methyl - 3 - sulfanilamidoisoxazole and trimethoxybenzyl pyrimidine |
| DE2065367C2 (de) * | 1969-03-06 | 1985-04-04 | The Wellcome Foundation Ltd., London | Verfahren zur Herstellung von 2,4- Diamino-5-benzylpyrimidinen |
| GB1261455A (en) * | 1969-03-06 | 1972-01-26 | Burroughs Wellcome Co | Improvements in or relating to substituted acrylonitriles |
| CH513181A (de) * | 1969-06-12 | 1971-09-30 | Hoffmann La Roche | Verfahren zur Herstellung von N-Oxyden von Benzylpyrimidinen |
| US3996356A (en) * | 1969-07-02 | 1976-12-07 | Hoffmann-La Roche Inc. | Composition containing 5-sulfanilamido-3,4-dimethylisoxazole and a trimethoxybenzyl pyrimidine |
| US3692787A (en) * | 1970-02-16 | 1972-09-19 | Burroughs Wellcome Co | Substituted 2,4-diamino-5-benzyl pyrimidines |
| US3684810A (en) * | 1970-03-11 | 1972-08-15 | Hoffmann La Roche | Process for 2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl) pyrimidine |
| BE792096A (fr) * | 1971-12-01 | 1973-05-30 | Hoffmann La Roche | Nouvelles benzylpyrimidines |
| US3993761A (en) * | 1971-12-01 | 1976-11-23 | Hoffmann-La Roche Inc. | Antibacterial compositions |
| BE795023A (fr) * | 1972-02-07 | 1973-08-06 | Hoffmann La Roche | Nouvelles benzylpyrimidines |
| IT1044231B (it) * | 1972-03-16 | 1980-03-20 | Hoffmann La Roche | Combinazione di sostanze attive utile per combattere infezioni da batteri gram positivi e gran negativi |
| DE2342213C3 (de) * | 1972-10-12 | 1979-10-18 | F. Hoffmann-La Roche & Co Ag, Basel (Schweiz) | Verwendung von potenzierten SuIf onamiden bei der Behandlung oder Verhinderung von Fischinfektionen |
| ZA738760B (en) * | 1972-12-21 | 1974-08-28 | Hoffmann La Roche | Process for the manufacture of benzyl pyrimidines |
| US4143227A (en) * | 1973-02-26 | 1979-03-06 | Hoffmann-La Roche Inc. | Process for substituted 5-benzyl-2,4-diamino-pyrimidines |
| US3931181A (en) * | 1973-07-27 | 1976-01-06 | Hoffmann-La Roche Inc. | 2,4-Diamino-5-benzylpyrimidines |
| CH591456A5 (it) * | 1973-09-12 | 1977-09-15 | Hoffmann La Roche | |
| CH591457A5 (it) * | 1973-11-08 | 1977-09-15 | Hoffmann La Roche | |
| US4076810A (en) * | 1973-11-08 | 1978-02-28 | Hoffmann-La Roche Inc. | Benzylpyrimidine antibacterial composition |
| JPS6119628B2 (it) * | 1973-11-08 | 1986-05-17 | Efu Hofuman Ra Roshu Unto Co Ag | |
| US4033962A (en) * | 1975-06-26 | 1977-07-05 | Hoffman-La Roche Inc. | 2,4-Diamino-pyrimidine derivatives and processes |
| NL7609171A (nl) * | 1975-08-29 | 1977-03-02 | Hoffmann La Roche | Werkwijze voor het bereiden van antibacte- riele middelen. |
| GB1582245A (en) * | 1976-06-09 | 1981-01-07 | Wellcome Found | Benzyl cyanoacetal derivatives and their conversion to pyrimidine derivatives |
| DE2635765C3 (de) * | 1976-08-09 | 1979-02-08 | Ludwig Heumann & Co Gmbh, 8500 Nuernberg | Verfahren zur Herstellung von 2,4-EMamino-5-(3',4'r5'-trimethoxybenzyl)-pyrimidin |
| LU77364A1 (it) * | 1977-05-18 | 1979-01-19 | ||
| JPS55102517A (en) * | 1979-01-30 | 1980-08-05 | Shionogi & Co Ltd | Preparation of sulfamethoxazole-trimethoprim complex for administration via body cavity |
| DE2944145A1 (de) * | 1979-11-02 | 1981-05-14 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von 2,4-diaminopyrimidin |
| JPS57109713A (en) * | 1980-12-26 | 1982-07-08 | Shionogi & Co Ltd | Pharmaceutical preparation of combined agent of sulfamethoxazole and trimethoprim for medication through celom |
| IT1138146B (it) * | 1981-08-11 | 1986-09-17 | Proter Spa | Processo per la produzione della 2,4-diammino-(3,5-dimetossi-4-metos sietossi-benzil)-pirimidina |
| FI64427C (fi) * | 1982-05-13 | 1989-11-08 | Uponor Nv | Lattiakaivo tai muu kuppimainen vesilukko. |
| HU197670B (en) * | 1986-02-28 | 1989-05-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing composition comprising 2,4-diamino-5-(3,4-dimethoxybenzyl)-pyrimidine or pharmaceutically suitable acid addition salt thereof as active ingredient |
| FR2595697B1 (fr) * | 1986-03-13 | 1988-07-08 | Rousselot Cie | Derives de benzyl-pyrimidine, leur procede de preparation ainsi que les compositions en contenant |
| US4857651A (en) * | 1987-07-29 | 1989-08-15 | American Cyanamid Company | α-(2,3-Di(C1 -C4 alkoxy)ethylamino)-β-cyanostyrene and β-nitrostyrene compounds useful as intermediates in the preparation of insecticidal, acaricidal and nematicidal arylpyrroles and method for the preparation thereof |
| US4996198A (en) * | 1988-07-11 | 1991-02-26 | Hoffmann-La Roche Inc. | Anticoccidial composition |
| US5135924A (en) * | 1989-01-03 | 1992-08-04 | Hoffmann-La Roche Inc. | Therapeutic treatment of animals with oral administration of ormetoprim-potentiated sulfonamides |
| US5158979A (en) * | 1989-04-19 | 1992-10-27 | New York University | Method and compositions for treating pneumocystic carini infections |
| US5258373A (en) * | 1991-07-17 | 1993-11-02 | Hoffmann-La Roche Inc. | Anticoccidial compositions |
| DE4333688C2 (de) * | 1993-10-02 | 2003-11-06 | Guenter Ege | Verfahren zur Herstellung von 3-Aryl-2-(dialkoxymethyl)-propannitrilen und ihre Umsetzung zu 5-Arylmethyl-2,4-diamino-pyrimidinen, insbesondere zu Trimethoprim |
| US5514681A (en) * | 1994-08-17 | 1996-05-07 | Virginia Tech Intellectual Properties, Inc. | Compositions and methods for controlling pest insects |
| TW438796B (en) * | 1996-05-15 | 2001-06-07 | Hoffmann La Roche | 2,4-diaminopyrimidine derivatives, the manufacture process thereof, and the antibiotically-active pharmaceutical composition containing the same |
| US20090162858A1 (en) * | 2007-09-18 | 2009-06-25 | Cornish Virginia W | Orthogonal chemical inducer of dimerization |
| BRPI0818675A2 (pt) * | 2007-10-29 | 2014-09-30 | Nippon Suisan Kaisha Ltd | Agente antiparasítico para peixes e método de controlar a proliferação de parasitas de peixes |
| TWI429397B (zh) * | 2009-04-27 | 2014-03-11 | Nippon Suisan Kaisha Ltd | 含有葉酸合成抑制劑及/或葉酸活性化抑制劑之組成物的用途 |
| FR3049861A1 (fr) | 2016-04-07 | 2017-10-13 | Univ Claude Bernard Lyon | Nouvelles compositions antivirales pour le traitement de la grippe |
| CN106083653A (zh) * | 2016-06-06 | 2016-11-09 | 江苏天和制药有限公司 | 奥美普林中间体肉桂腈的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049544A (en) * | 1962-08-14 | Method for the preparation of | ||
| US2628236A (en) * | 1953-02-10 | S-benzyl | ||
| US2658897A (en) * | 1951-06-27 | 1953-11-10 | Burroughs Wellcome Co | 2, 4-diamino-5-benzyl pyrimidines |
| GB734801A (en) * | 1953-03-06 | 1955-08-10 | Wellcome Found | Improvements in and relating to derivatives of pyrimidine and the manufacture thereof |
| US2783178A (en) * | 1954-06-22 | 1957-02-26 | American Scient Lab Inc | Stable concentrated sulfaquinoxaline solutions and method for preparing |
| US2823160A (en) * | 1955-03-29 | 1958-02-11 | Whitmoyer Lab Inc | Substituted pyrimidines compositions for chemotherapy of coccidiosis |
| US2909522A (en) * | 1957-02-21 | 1959-10-20 | Burroughs Wellcome Co | Trialkoxybenzylpyrimidines and method |
| DE1303727B (de) * | 1959-09-03 | 1976-02-05 | Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London | Alpha-Arylidensubstituierte Propioni-Irile |
| US3085937A (en) * | 1960-11-21 | 1963-04-16 | Shionogi & Co | Method of combating coccidiosis with sulfonamide compositions |
| US3485840A (en) * | 1964-11-12 | 1969-12-23 | Hoffmann La Roche | 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes |
-
1965
- 1965-05-07 US US454172A patent/US3485840A/en not_active Expired - Lifetime
- 1965-06-02 US US460834A patent/US3461206A/en not_active Expired - Lifetime
- 1965-07-09 US US470917A patent/US3341541A/en not_active Expired - Lifetime
- 1965-10-15 CH CH1427165A patent/CH467784A/de unknown
- 1965-10-20 DE DE19651545966 patent/DE1545966A1/de active Pending
- 1965-10-21 IL IL24497A patent/IL24497A/en unknown
- 1965-10-21 IL IL24498A patent/IL24498A/xx unknown
- 1965-10-22 CH CH1464865A patent/CH467270A/de unknown
- 1965-10-25 DE DE1545967A patent/DE1545967C3/de not_active Expired
- 1965-10-27 IL IL6532695A patent/IL32695A/xx unknown
- 1965-10-27 IL IL6532696A patent/IL32696A/en unknown
- 1965-10-27 IL IL24534A patent/IL24534A/xx unknown
- 1965-10-27 IL IL32694A patent/IL32694A/xx unknown
- 1965-10-27 IL IL32697A patent/IL32697A/xx unknown
- 1965-10-28 DK DK554065AA patent/DK125553B/da unknown
- 1965-10-30 FR FR36822A patent/FR5411M/fr not_active Expired
- 1965-11-01 FI FI2606/65A patent/FI43251B/fi active
- 1965-11-02 NL NL6514178A patent/NL6514178A/xx unknown
- 1965-11-05 GB GB58793/67A patent/GB1132085A/en not_active Expired
- 1965-11-05 GB GB58791/67A patent/GB1132083A/en not_active Expired
- 1965-11-05 GB GB46937/65A patent/GB1062508A/en not_active Expired
- 1965-11-05 GB GB46935/65A patent/GB1132082A/en not_active Expired
- 1965-11-05 GB GB58792/67A patent/GB1132084A/en not_active Expired
- 1965-11-05 GB GB46936/65A patent/GB1133766A/en not_active Expired
- 1965-11-05 GB GB58794/67A patent/GB1132086A/en not_active Expired
- 1965-11-08 BE BE671983D patent/BE671983A/xx not_active IP Right Cessation
- 1965-11-08 BE BE671982D patent/BE671982A/xx unknown
- 1965-11-08 BE BE671981D patent/BE671981A/xx unknown
- 1965-11-08 NL NL6514472A patent/NL6514472A/xx unknown
- 1965-11-09 BR BR174670/65A patent/BR6574670D0/pt unknown
- 1965-11-09 BR BR174667/65A patent/BR6574667D0/pt unknown
- 1965-11-09 BR BR174668/65A patent/BR6574668D0/pt unknown
- 1965-11-11 NO NO160436A patent/NO119948B/no unknown
- 1965-11-11 NO NO160437A patent/NO115741B/no unknown
- 1965-11-11 DK DK581065AA patent/DK115847B/da unknown
- 1965-11-12 SE SE3420/69A patent/SE346314B/xx unknown
- 1965-11-12 SE SE14670/65A patent/SE326185B/xx unknown
- 1965-11-12 SE SE14669/65A patent/SE327122B/xx unknown
- 1965-11-12 NL NL6514743.A patent/NL163213C/xx not_active IP Right Cessation
- 1965-11-12 SE SE14668/65A patent/SE311160B/xx unknown
- 1965-11-12 IT IT25233/65A patent/IT1058251B/it active
-
1967
- 1967-12-31 MY MY1967159A patent/MY6700159A/xx unknown
-
1972
- 1972-12-30 MY MY71/72A patent/MY7200071A/xx unknown
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