DK149885B - Analogifremgangsmaade til fremstilling af s-oxyder af 5-halogenpyrimidin-2-sulfider eller fysiologisk acceptable salte deraf - Google Patents

Analogifremgangsmaade til fremstilling af s-oxyder af 5-halogenpyrimidin-2-sulfider eller fysiologisk acceptable salte deraf Download PDF

Info

Publication number: DK149885B
Authority: DK; Denmark
Prior art keywords: group; mmol; alkyl; solution; chloropyrimidine
Prior art date: 1980-01-10

Application number

DK008081AA

Other languages

Danish (da)

English (en)

Other versions

DK8081A (da

Inventor

Tore Benneche

Mikkel Josef Gacek

Kjell Undheim

Original Assignee

Nyegaard & Co As

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-01-10

Filing date

1981-01-09

Publication date

1986-10-20

1981-01-09 Application filed by Nyegaard & Co As filed Critical Nyegaard & Co As

1981-07-11 Publication of DK8081A publication Critical patent/DK8081A/da

1986-10-20 Publication of DK149885B publication Critical patent/DK149885B/da

Links

150000003839 salts Chemical class 0.000 title claims abstract description 20
229910052736 halogen Inorganic materials 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 7
238000000034 method Methods 0.000 title description 22
150000001875 compounds Chemical class 0.000 claims abstract description 78
-1 nitro, hydroxy Chemical group 0.000 claims abstract description 61
229920006395 saturated elastomer Polymers 0.000 claims abstract description 24
125000003118 aryl group Chemical group 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 6
230000002378 acidificating effect Effects 0.000 claims abstract description 5
125000004429 atom Chemical group 0.000 claims abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
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125000000217 alkyl group Chemical group 0.000 claims description 22
239000000460 chlorine Chemical group 0.000 claims description 21
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229910052801 chlorine Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 6
229910052717 sulfur Chemical group 0.000 claims description 5
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229910052757 nitrogen Inorganic materials 0.000 claims description 4
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125000005236 alkanoylamino group Chemical group 0.000 claims description 2
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LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 24
238000007254 oxidation reaction Methods 0.000 abstract description 15
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239000000543 intermediate Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000002904 solvent Substances 0.000 description 21
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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239000002253 acid Substances 0.000 description 11
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YQPFSEFXQRQMHG-UHFFFAOYSA-N 5-chloro-1h-pyrimidine-2-thione Chemical compound SC1=NC=C(Cl)C=N1 YQPFSEFXQRQMHG-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
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239000011734 sodium Substances 0.000 description 9
150000003462 sulfoxides Chemical class 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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230000005764 inhibitory process Effects 0.000 description 7
230000031864 metaphase Effects 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
PGBONSLCITYXTJ-UHFFFAOYSA-N 5-chloro-2-(chloromethylsulfanyl)pyrimidine Chemical compound ClCSC1=NC=C(Cl)C=N1 PGBONSLCITYXTJ-UHFFFAOYSA-N 0.000 description 6
230000006820 DNA synthesis Effects 0.000 description 6
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HUCDDPXTOUAWRA-UHFFFAOYSA-N 5-chloro-2-(iodomethylsulfanyl)pyrimidine Chemical compound ClC1=CN=C(SCI)N=C1 HUCDDPXTOUAWRA-UHFFFAOYSA-N 0.000 description 5
SMCBWPSPCSKMAZ-UHFFFAOYSA-N 5-chloro-2-(iodomethylsulfonyl)pyrimidine Chemical compound ClC1=CN=C(S(=O)(=O)CI)N=C1 SMCBWPSPCSKMAZ-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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230000028993 immune response Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZPVFWDOODMTJSO-UHFFFAOYSA-N methyl 5-chloro-2-methylsulfonylpyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(S(C)(=O)=O)=NC=C1Cl ZPVFWDOODMTJSO-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000000394 mitotic effect Effects 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
238000004264 monolayer culture Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-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
238000000746 purification Methods 0.000 description 1
125000003132 pyranosyl group Chemical group 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 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
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid 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
238000004809 thin layer chromatography Methods 0.000 description 1
150000003571 thiolactams Chemical class 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
IQQAWKBHFPJYDR-UHFFFAOYSA-N thiophen-2-ylmethyl 2-(5-bromo-4,6-dimethylpyrimidin-2-yl)sulfanylacetate Chemical compound CC1=C(Br)C(C)=NC(SCC(=O)OCC=2SC=CC=2)=N1 IQQAWKBHFPJYDR-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
210000004881 tumor cell Anatomy 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Glass Compositions (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Compositions Of Macromolecular Compounds (AREA)
Saccharide Compounds (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)

DK008081AA 1980-01-10 1981-01-09 Analogifremgangsmaade til fremstilling af s-oxyder af 5-halogenpyrimidin-2-sulfider eller fysiologisk acceptable salte deraf DK149885B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8000802		1980-01-10
GB8000802		1980-01-10

Publications (2)

Publication Number	Publication Date
DK8081A DK8081A (da)	1981-07-11
DK149885B true DK149885B (da)	1986-10-20

Family

ID=10510550

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK008081AA DK149885B (da)	1980-01-10	1981-01-09	Analogifremgangsmaade til fremstilling af s-oxyder af 5-halogenpyrimidin-2-sulfider eller fysiologisk acceptable salte deraf

Country Status (12)

Country	Link
US (1)	US4423047A (de)
EP (1)	EP0033195B1 (de)
JP (1)	JPS56154467A (de)
AT (1)	ATE16799T1 (de)
AU (1)	AU549117B2 (de)
CA (1)	CA1168240A (de)
DE (1)	DE3173080D1 (de)
DK (1)	DK149885B (de)
ES (2)	ES8205782A1 (de)
NO (1)	NO810064L (de)
NZ (1)	NZ195992A (de)
ZA (1)	ZA81140B (de)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
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EP0056319B1 (de) *	1981-01-09	1986-04-16	NYEGAARD & CO. A/S	Substituierte Pyrimidin-2-one und deren Salze
JPS58159479A (ja) *	1982-02-24	1983-09-21	ニユエガ−ド・アンド・コンパニ−・アクシエ／セルカペト	置換されたピリミジン−２−オン化合物
JPH0739394B2 (ja) *	1985-05-30	1995-05-01	住友化学工業株式会社	含窒素複素環化合物およびそれを有効成分として含有する有害生物防除剤
JPS63179840A (ja) *	1986-07-24	1988-07-23	Yamanouchi Pharmaceut Co Ltd	新規化学物質
US4808591A (en) *	1988-02-16	1989-02-28	Pfizer Inc.	Antiulcer 8-(2-pyrimidylsulfinyl)quinolines
DE3912155A1 (de) *	1988-09-24	1990-03-29	Bayer Ag	Schaedlingsbekaempfungsmittel auf basis von 2-halogenalkylthio-substituierten pyrimidin-derivaten
AU7742491A (en) *	1990-04-12	1991-11-11	Stereo-Chemical Genetics, Inc.	Synthetic piperidinediones with cytostatic activity
GB9106609D0 (en) *	1991-03-28	1991-05-15	Ici Plc	Heterocyclic compounds
GB9205484D0 (en) *	1991-03-28	1992-04-29	Ici Plc	Heterocyclic compounds
GB9205487D0 (en) *	1991-03-28	1992-04-29	Ici Plc	Heterocyclic compounds
GB9219635D0 (en) *	1992-09-16	1992-10-28	Ici Plc	Heterocyclic compounds
DE19622270A1 (de) *	1996-06-03	1997-12-04	Basf Ag	Pyrimidin-4-carbonsäureamide
US6268310B1 (en) *	1997-01-28	2001-07-31	Nippon Soda Co., Ltd.	Oxazole derivative, process for producing the same, and herbicide
WO2000014095A1 (en)	1998-09-09	2000-03-16	Metabasis Therapeutics, Inc.	Novel heteroaromatic inhibitors of fructose 1,6-bisphosphatase
AU2145500A (en) *	1998-11-30	2000-06-19	Ishihara Sangyo Kaisha Ltd.	A meta-nitro phenol derivative and a process for producing it
US6313072B1 (en) *	1999-02-18	2001-11-06	American Cyanamid Company	Herbicidal 2-aryloxy-or 2-arylthio-6-arylpyrimidines
US7563774B2 (en)	2000-06-29	2009-07-21	Metabasis Therapeutics, Inc.	Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes
US7138404B2 (en) *	2001-05-23	2006-11-21	Hoffmann-La Roche Inc.	4-aminopyrimidine derivatives
DE10154075A1 (de) *	2001-11-02	2003-05-15	Bayer Cropscience Ag	Substituierte Pyrimidine
JP5448164B2 (ja) *	2006-07-28	2014-03-19	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	Ｃｂ２受容体を変調する化合物
US9364191B2 (en)	2013-02-11	2016-06-14	University Of Rochester	Method and apparatus of spectral differential phase-contrast cone-beam CT and hybrid cone-beam CT
AU2015206757A1 (en)	2014-01-16	2016-06-30	Fmc Corporation	Pyrimidinyloxy benzene derivatives as herbicides
TWI713530B (zh)	2015-06-05	2020-12-21	美商艾佛艾姆希公司	作為除草劑之嘧啶氧基苯衍生物
GB201514649D0 (en) *	2015-08-18	2015-09-30	Medical Res Council	2-Sulfonylpyrimidines
BR112019022493B1 (pt)	2017-05-02	2024-01-16	Fmc Corporation	Composto, composições herbicidas, misturas herbicidas e métodos para controlar o crescimento de vegetação indesejada

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US3112316A (en) *		1963-11-26		Z-o-chlohobenzylmercapto-x-dimethyl-
US2876224A (en) *	1957-08-07	1959-03-03	American Home Prod	Basic esters of substituted pyrimidine-4-carboxylic acids and their preparation
DE2455582A1 (de) *	1974-11-23	1976-05-26	Hoechst Ag	Verfahren zur herstellung von (1-alkyl-5-nitro-imidazolyl-2-alkyl)heteroaryl-sulfiden
GB1561290A (en)	1975-10-16	1980-02-20	Nyegaard & Co As	Pyrimid - 2 - ones
US4248618A (en) *	1977-05-06	1981-02-03	Ici Australia Limited	Derivatives of (pyrimidyloxy)phenoxy-alkanecarboxylic acid and herbicidal compositions thereof
NZ188244A (en) *	1977-09-13	1981-04-24	Ici Australia Ltd	2-substituted pyrimidines compositions growth regulating processes

1981
- 1981-01-09 ES ES498406A patent/ES8205782A1/es not_active Expired
- 1981-01-09 ZA ZA00810140A patent/ZA81140B/xx unknown
- 1981-01-09 NO NO810064A patent/NO810064L/no unknown
- 1981-01-09 US US06/223,760 patent/US4423047A/en not_active Expired - Fee Related
- 1981-01-09 EP EP81300098A patent/EP0033195B1/de not_active Expired
- 1981-01-09 JP JP200181A patent/JPS56154467A/ja active Pending
- 1981-01-09 AT AT81300098T patent/ATE16799T1/de not_active IP Right Cessation
- 1981-01-09 DE DE8181300098T patent/DE3173080D1/de not_active Expired
- 1981-01-09 NZ NZ195992A patent/NZ195992A/xx unknown
- 1981-01-09 DK DK008081AA patent/DK149885B/da unknown
- 1981-01-09 AU AU66130/81A patent/AU549117B2/en not_active Expired - Fee Related
- 1981-01-12 CA CA000368409A patent/CA1168240A/en not_active Expired
1982
- 1982-01-02 ES ES508498A patent/ES508498A0/es active Granted

Also Published As

Publication number	Publication date
ZA81140B (en)	1982-02-24
ES8304947A1 (es)	1983-03-16
ES498406A0 (es)	1982-08-01
DE3173080D1 (en)	1986-01-16
NZ195992A (en)	1983-11-30
DK8081A (da)	1981-07-11
NO810064L (no)	1981-07-13
EP0033195A1 (de)	1981-08-05
AU6613081A (en)	1981-07-16
US4423047A (en)	1983-12-27
CA1168240A (en)	1984-05-29
ES8205782A1 (es)	1982-08-01
ATE16799T1 (de)	1985-12-15
EP0033195B1 (de)	1985-12-04
JPS56154467A (en)	1981-11-30
ES508498A0 (es)	1983-03-16
AU549117B2 (en)	1986-01-16

Publication	Publication Date	Title
US4423047A (en)	1983-12-27	Pyrimidine-2-sulphides and their S-oxides for use in medicine and methods of use therefor, pharmaceutical compositions containing them, processes for their preparation and per se novel sulphides and S-oxides
US6057305A (en)	2000-05-02	Antiretroviral enantiomeric nucleotide analogs
SU1052161A3 (ru)	1983-10-30	Способ получени производных тиоэтиановой кислоты
EP0454427B1 (de)	1995-12-06	Antiretrovirale Basen
DE68918804T2 (de)	1995-02-23	Acyclische 6-substituierte pyrimidin nukleosid-abkömmlinge und antivirale mittel, die dieselben als aktive mittel enthalten.
JP2013047245A (ja)	2013-03-07	ピリジン誘導体の調製方法
DE69033998T2 (de)	2003-05-08	6-Substituierte Acylopyrimidin-Nucleoside-Derivate und diese als wirksamen Stoff enthaltende Antivirusmittel
EP0138656B1 (de)	1989-09-27	Zyklische Purin- und Pyrimidin-Acyclonucleosiden, ihre Herstellung und ihre Anwendung in anti-viralen Zusammensetzungen
DK148538B (da)	1985-07-29	Analogifremgangsmaade til fremstilling af 2,3-substituerede 4-pyroner
ANGIER et al.	1961	Alkylation of 2-Amino-4-hydroxypyrimidines with Acrylonitrile and with Dimethyl Sulfate: Two Pyrimido [1, 2-α] pyrimidinediones
Szabo et al.	1970	Reaction of 5-bromouracil derivatives with sulfur nucleophiles, and a novel synthetic route to 5-sulfur-substituted uracils and nucleotides
NO163692B (no)	1990-03-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive oksazafosforin-4-tio-alkansulfonsyrer og salter derav.
NO812431L (no)	1982-01-18	Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater.
NZ221293A (en)	1990-01-29	Substituted uridine derivatives and pharmaceutical compositions
NO160514B (no)	1989-01-16	Analogifremgangsm te for fremstilling av farmasoeytisk aktive pyrimid-2-on-derivater.
KR100233068B1 (ko)	1999-12-01	2-치환된 4,6-디알콕시피리미딘의 제조방법
US4478839A (en)	1984-10-23	Substituted pyrimid-2-ones, the salts thereof, processes for their preparation and pharmaceutical compositions containing them
NO823445L (no)	1983-07-25	Substituerte tiazolidinylestere av mineralsyrer
PT93852B (pt)	1996-08-30	Processo para a preparacao de purinil e pirimidinil-tetra-hidrofuranos com accao antiviral
KR20020040657A (ko)	2002-05-30	Ｍｋｃ-442의 제조 방법
US4539324A (en)	1985-09-03	Substituted pyrimidin-2-ones and the salts thereof
NO783775L (no)	1979-05-11	2,4-diamino-5-benzylpyrimidiner og fremgangsmaate ved fremstilling av disse
SU884568A3 (ru)	1981-11-23	Способ получени (арилалкил) алкановых кислот
JPH0556348B2 (de)	1993-08-19
CA1200495A (en)	1986-02-11	Pyrimidine-2-sulphides and their s-oxides for use in medicine and methods of use therefor, pharmaceutical compositions containing them, processes for their preparation and suchcompounds when novel per se