NO810064L - Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav - Google Patents

Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav

Info

Publication number: NO810064L
Authority: NO; Norway
Prior art keywords: group; formula; chloropyrimidine; mmol; solution
Prior art date: 1980-01-10

Application number

NO810064A

Other languages

English (en)

Norwegian (no)

Inventor

Tore Bennecke

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

1981-07-13

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

1981-07-13 Publication of NO810064L publication Critical patent/NO810064L/no

Links

238000000034 method Methods 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 15
150000001875 compounds Chemical class 0.000 claims abstract description 99
-1 nitro, hydroxy Chemical group 0.000 claims abstract description 47
229920006395 saturated elastomer Polymers 0.000 claims abstract description 26
125000003118 aryl group Chemical group 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 21
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
125000001424 substituent group Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 11
230000002378 acidificating effect Effects 0.000 claims abstract description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004122 cyclic group Chemical group 0.000 claims abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 5
125000001302 tertiary amino group Chemical group 0.000 claims abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
125000004442 acylamino group Chemical group 0.000 claims abstract description 4
125000002015 acyclic group Chemical group 0.000 claims abstract description 3
125000003368 amide group Chemical group 0.000 claims abstract description 3
125000004429 atom Chemical group 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims description 23
229910052801 chlorine Inorganic materials 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
150000003573 thiols Chemical class 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
CFMHODUFAULRDE-UHFFFAOYSA-N 2-benzylsulfinyl-5-chloropyrimidine Chemical compound N1=CC(Cl)=CN=C1S(=O)CC1=CC=CC=C1 CFMHODUFAULRDE-UHFFFAOYSA-N 0.000 claims description 3
WBFKVUDHNWXMGZ-UHFFFAOYSA-N 2-benzylsulfonyl-5-bromopyrimidine Chemical compound N1=CC(Br)=CN=C1S(=O)(=O)CC1=CC=CC=C1 WBFKVUDHNWXMGZ-UHFFFAOYSA-N 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
230000000087 stabilizing effect Effects 0.000 claims description 2
125000005504 styryl group Chemical group 0.000 claims description 2
150000007944 thiolates Chemical class 0.000 claims description 2
UTRLCQDZBAISRZ-UHFFFAOYSA-N 4-(5-chloropyrimidin-2-yl)sulfonylbut-3-en-2-one Chemical compound CC(=O)C=CS(=O)(=O)C1=NC=C(Cl)C=N1 UTRLCQDZBAISRZ-UHFFFAOYSA-N 0.000 claims 1
MTQAMKPQZOODHH-UHFFFAOYSA-N 5-chloro-2-(2-phenylethenylsulfonyl)pyrimidine Chemical compound N1=CC(Cl)=CN=C1S(=O)(=O)C=CC1=CC=CC=C1 MTQAMKPQZOODHH-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
238000007254 oxidation reaction Methods 0.000 abstract description 23
230000003647 oxidation Effects 0.000 abstract description 22
238000006243 chemical reaction Methods 0.000 abstract description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 13
230000002159 abnormal effect Effects 0.000 abstract description 12
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 11
125000004043 oxo group Chemical group O=* 0.000 abstract description 5
125000000714 pyrimidinyl group Chemical group 0.000 abstract description 3
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 abstract description 3
230000004663 cell proliferation Effects 0.000 abstract 1
238000006073 displacement reaction Methods 0.000 abstract 1
238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 202
239000000243 solution Substances 0.000 description 180
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
239000000203 mixture Substances 0.000 description 94
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
238000005481 NMR spectroscopy Methods 0.000 description 77
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
239000002904 solvent Substances 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000010992 reflux Methods 0.000 description 23
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
YQPFSEFXQRQMHG-UHFFFAOYSA-N 5-chloro-1h-pyrimidine-2-thione Chemical compound SC1=NC=C(Cl)C=N1 YQPFSEFXQRQMHG-UHFFFAOYSA-N 0.000 description 17
150000003457 sulfones Chemical class 0.000 description 16
210000004027 cell Anatomy 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000011734 sodium Substances 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
150000003462 sulfoxides Chemical class 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
HUCDDPXTOUAWRA-UHFFFAOYSA-N 5-chloro-2-(iodomethylsulfanyl)pyrimidine Chemical compound ClC1=CN=C(SCI)N=C1 HUCDDPXTOUAWRA-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
230000010261 cell growth Effects 0.000 description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
125000003396 thiol group Chemical group [H]S* 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000002198 insoluble material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
PGBONSLCITYXTJ-UHFFFAOYSA-N 5-chloro-2-(chloromethylsulfanyl)pyrimidine Chemical compound ClCSC1=NC=C(Cl)C=N1 PGBONSLCITYXTJ-UHFFFAOYSA-N 0.000 description 5
KCFLVIFHMXKXSG-UHFFFAOYSA-N 5-chloro-2-prop-2-ynylsulfanylpyrimidine Chemical compound ClC1=CN=C(SCC#C)N=C1 KCFLVIFHMXKXSG-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000022131 cell cycle Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
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 5
229930192474 thiophene Natural products 0.000 description 5
ZNMVGPFFXNRTKV-UHFFFAOYSA-N 2-benzylsulfanyl-5-chloropyrimidine Chemical compound N1=CC(Cl)=CN=C1SCC1=CC=CC=C1 ZNMVGPFFXNRTKV-UHFFFAOYSA-N 0.000 description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
XPGIBDJXEVAVTO-UHFFFAOYSA-N 5-bromo-2-chloropyrimidine Chemical compound ClC1=NC=C(Br)C=N1 XPGIBDJXEVAVTO-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
230000001766 physiological effect Effects 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
LXOANVAJTYXINB-UHFFFAOYSA-N 2-benzylsulfanyl-5-bromopyrimidine Chemical compound N1=CC(Br)=CN=C1SCC1=CC=CC=C1 LXOANVAJTYXINB-UHFFFAOYSA-N 0.000 description 3
MDZCNJHECVPINP-UHFFFAOYSA-N 5-bromo-2-chloro-4,6-dimethylpyrimidine Chemical compound CC1=NC(Cl)=NC(C)=C1Br MDZCNJHECVPINP-UHFFFAOYSA-N 0.000 description 3
GIUNKHSQPXBIFE-UHFFFAOYSA-N 5-chloro-2-(iodomethylsulfinyl)pyrimidine Chemical compound ClC1=CN=C(S(=O)CI)N=C1 GIUNKHSQPXBIFE-UHFFFAOYSA-N 0.000 description 3
SOUFZTWGFMIRQK-UHFFFAOYSA-N 5-chloro-2-[(4-chlorophenoxy)methylsulfanyl]pyrimidine Chemical compound C1=CC(Cl)=CC=C1OCSC1=NC=C(Cl)C=N1 SOUFZTWGFMIRQK-UHFFFAOYSA-N 0.000 description 3
PVQBPCUDJZNALN-UHFFFAOYSA-N 5-chloro-2-[(5-chloropyrimidin-2-yl)oxymethylsulfanyl]pyrimidine Chemical compound N1=CC(Cl)=CN=C1OCSC1=NC=C(Cl)C=N1 PVQBPCUDJZNALN-UHFFFAOYSA-N 0.000 description 3
YYQOYLZOMFNKKG-UHFFFAOYSA-N 5-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=C(Cl)C=N1 YYQOYLZOMFNKKG-UHFFFAOYSA-N 0.000 description 3
YNTUFGHUELCCQR-UHFFFAOYSA-N 5-chloro-2-phenylsulfanylpyrimidine Chemical compound N1=CC(Cl)=CN=C1SC1=CC=CC=C1 YNTUFGHUELCCQR-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
PSRGBWDWQPDGPM-UHFFFAOYSA-N 1-chloro-3-(5-chloropyrimidin-2-yl)sulfanylpropan-2-ol Chemical compound ClCC(O)CSC1=NC=C(Cl)C=N1 PSRGBWDWQPDGPM-UHFFFAOYSA-N 0.000 description 2
CEJAHXLRNZJPQH-UHFFFAOYSA-N 2,5-dichloropyrimidine Chemical compound ClC1=CN=C(Cl)N=C1 CEJAHXLRNZJPQH-UHFFFAOYSA-N 0.000 description 2
IEQKGDZZLKQDPY-UHFFFAOYSA-N 2-benzylsulfanyl-5-bromo-4,6-dimethylpyrimidine Chemical compound CC1=C(Br)C(C)=NC(SCC=2C=CC=CC=2)=N1 IEQKGDZZLKQDPY-UHFFFAOYSA-N 0.000 description 2
DONRDSVBRXKNPO-UHFFFAOYSA-N 2-benzylsulfonyl-5-chloropyrimidine Chemical compound N1=CC(Cl)=CN=C1S(=O)(=O)CC1=CC=CC=C1 DONRDSVBRXKNPO-UHFFFAOYSA-N 0.000 description 2
DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 2
PELYSUXCWVOHPG-UHFFFAOYSA-N 2-iodo-n-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1NC(=O)CI PELYSUXCWVOHPG-UHFFFAOYSA-N 0.000 description 2
RJWGGLVUYJLKRT-UHFFFAOYSA-N 3-(5-chloropyrimidin-2-yl)sulfonylpentan-3-ylphosphonic acid Chemical compound CCC(CC)(P(O)(O)=O)S(=O)(=O)C1=NC=C(Cl)C=N1 RJWGGLVUYJLKRT-UHFFFAOYSA-N 0.000 description 2
GJMCPBUCFOSOKN-UHFFFAOYSA-N 5-bromo-2-(thiophen-2-ylmethylsulfanyl)pyrimidine Chemical compound N1=CC(Br)=CN=C1SCC1=CC=CS1 GJMCPBUCFOSOKN-UHFFFAOYSA-N 0.000 description 2
CPLBOQSYONKFSP-UHFFFAOYSA-N 5-bromo-2-phenylsulfanylpyrimidine Chemical compound N1=CC(Br)=CN=C1SC1=CC=CC=C1 CPLBOQSYONKFSP-UHFFFAOYSA-N 0.000 description 2
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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

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

NO810064A 1980-01-10 1981-01-09 Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav NO810064L (no)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
NO810064L true NO810064L (no)	1981-07-13

Family

ID=10510550

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO810064A NO810064L (no)	1980-01-10	1981-01-09	Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav

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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US4596870A (en) *	1981-01-09	1986-06-24	Nyegaard & Co. A.S.	Substituted pyrimidin-2-ones and the salts thereof
EP0087326B1 (de) *	1982-02-24	1987-05-13	Nycomed As	Substituierte Pyrimidin-2-one und deren Salze
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
WO1991016309A1 (en) *	1990-04-12	1991-10-31	University Of Georgia Research Foundation, Inc.	Synthetic piperidinediones with cytostatic activity
GB9106609D0 (en) *	1991-03-28	1991-05-15	Ici Plc	Heterocyclic compounds
EP0506270A1 (de) *	1991-03-28	1992-09-30	Zeneca Limited	Nematozide Pyrimidinverbindungen
EP0506269A1 (de) *	1991-03-28	1992-09-30	Zeneca Limited	Nematozide Pyrimidinverbindungen
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
CZ297264B6 (cs)	1998-09-09	2006-10-11	Metabasis Therapeutics, Inc.	Nové heteroaromatické inhibitory fruktóza-1,6-bisfosfatázy
EP1144380A4 (de) *	1998-11-30	2003-11-26	Ishihara Sangyo Kaisha	Meta-nitrophenol-derivat und ein verfahren zu seiner herstellung
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
WO2008014199A2 (en) *	2006-07-28	2008-01-31	Boehringer Ingelheim International Gmbh	Sulfonyl compounds which modulate the cb2 receptor
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
WO2015108779A1 (en)	2014-01-16	2015-07-23	E. I. Du Pont De Nemours And Company	Pyrimidinyloxy benzene derivatives as herbicides
TWI828952B (zh)	2015-06-05	2024-01-11	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
EP3619206B1 (de)	2017-05-02	2024-02-14	FMC Corporation	Pyrimidinyloxybenzo-kondensierte verbindungen als herbizide

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Publication number	Priority date	Publication date	Assignee	Title
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 AU AU66130/81A patent/AU549117B2/en not_active Expired - Fee Related
- 1981-01-09 NZ NZ195992A patent/NZ195992A/xx unknown
- 1981-01-09 DE DE8181300098T patent/DE3173080D1/de not_active Expired
- 1981-01-09 DK DK008081AA patent/DK149885B/da unknown
- 1981-01-09 JP JP200181A patent/JPS56154467A/ja active Pending
- 1981-01-09 ES ES498406A patent/ES8205782A1/es not_active Expired
- 1981-01-09 AT AT81300098T patent/ATE16799T1/de not_active IP Right Cessation
- 1981-01-09 US US06/223,760 patent/US4423047A/en not_active Expired - Fee Related
- 1981-01-09 NO NO810064A patent/NO810064L/no unknown
- 1981-01-09 ZA ZA00810140A patent/ZA81140B/xx unknown
- 1981-01-09 EP EP81300098A patent/EP0033195B1/de not_active Expired
- 1981-01-12 CA CA000368409A patent/CA1168240A/en not_active Expired
1982
- 1982-01-02 ES ES508498A patent/ES8304947A1/es not_active Expired

Also Published As

Publication number	Publication date
US4423047A (en)	1983-12-27
EP0033195A1 (de)	1981-08-05
EP0033195B1 (de)	1985-12-04
DE3173080D1 (en)	1986-01-16
NZ195992A (en)	1983-11-30
ES508498A0 (es)	1983-03-16
ATE16799T1 (de)	1985-12-15
DK149885B (da)	1986-10-20
ES498406A0 (es)	1982-08-01
ES8205782A1 (es)	1982-08-01
DK8081A (da)	1981-07-11
CA1168240A (en)	1984-05-29
ZA81140B (en)	1982-02-24
JPS56154467A (en)	1981-11-30
ES8304947A1 (es)	1983-03-16
AU6613081A (en)	1981-07-16
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
SU1052161A3 (ru)	1983-10-30	Способ получени производных тиоэтиановой кислоты
EP0257781B1 (de)	1991-09-18	Verfahren zur Herstellung von Thiazolidinedion-Derivaten
NO150839B (no)	1984-09-17	Analogifremgangsmaate ved fremstilling av terapeutisk aktivt 5-(4-pyridyl-6-(4-fluorfenyl)-2,3-dihydroimidazo-(2,1-b)-tiazol
Lee et al.	1985	Syntheses and reactions of 2‐halo‐5‐thiazolecarboxylates
NO148926B (no)	1983-10-03	Analogifremgangsmaate til fremstilling av terapeutisk aktive, nye merkaptoimidazolderivater
Szabo et al.	1970	Reaction of 5-bromouracil derivatives with sulfur nucleophiles, and a novel synthetic route to 5-sulfur-substituted uracils and nucleotides
US4874877A (en)	1989-10-17	Process for optically active 3-(methane-sulfonyloxy)thiolane and analogs
NO820881L (no)	1982-09-20	Fremgangsmaate til fremstilling av nye tiazolderivater.
EP0171739B1 (de)	1990-01-10	Imidazo[1,5-a]pyrimidinderivate und Verfahren zu ihrer Herstellung
KR910005850B1 (ko)	1991-08-05	이미다조[1,5-a]피리미딘 유도체의 제조방법
CA1091695A (en)	1980-12-16	4-alkylthio-2-trifluoromethylalkane-sulfonanilides and derivatives thereof
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
US4496568A (en)	1985-01-29	Antiinflammatory thieno [2,3-c]pyridine derivatives
EP0319170B1 (de)	1993-03-17	Acyl-Derivate von Hydroxy-Pyrimidinen
US6777575B2 (en)	2004-08-17	Process for the preparation of 2-alkylthio benzoic acid derivatives
ES2203762T3 (es)	2004-04-16	Piridinas intermedias utiles en la sintesis de agonistas del receptor adrenergico beta.
NO823075L (no)	1983-03-14	Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater
NO161440B (no)	1989-05-08	Analogifremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-oner.
JPH0556348B2 (de)	1993-08-19
SE436571B (sv)	1985-01-07	Imidazolylmetyltrifenylfosfoniumderivat anvendbar som mellanprodukt for framstellning av histamin h?712-antagonister
US4937329A (en)	1990-06-26	Production of 2,3'-anhydro-2'-deoxyuridine derivatives
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
Christov et al.	2002	Alkatrienyl sulfoxides and sulfones. Part II.[1](5-methyl-1, 3, 4-hexatriene-3-yl) phenyl sulfoxide-synthesis and electrophile-promoted cyclization reactions