IL26578A - Pethridine compounds and their preparation - Google Patents

Pethridine compounds and their preparation

Info

Publication number: IL26578A
Authority: IL; Israel
Prior art keywords: amino; diamino; chloro; mole; preparation
Prior art date: 1965-10-04

Application number

IL2657866A

Other languages

English (en)

Hebrew (he)

Original Assignee

Merck & Co Inc

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.)

1965-10-04

Filing date

1966-09-26

Publication date

1970-11-30

1966-09-26 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1970-11-30 Publication of IL26578A publication Critical patent/IL26578A/en

Links

238000002360 preparation method Methods 0.000 title description 43
125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 title 1
238000000034 method Methods 0.000 claims description 40
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
230000008569 process Effects 0.000 claims description 11
239000000376 reactant Substances 0.000 claims description 11
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 10
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 10
150000002825 nitriles Chemical class 0.000 claims description 9
PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical group N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
239000000047 product Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 27
-1 alkali metal salt Chemical class 0.000 description 24
238000001914 filtration Methods 0.000 description 24
239000007787 solid Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
125000001246 bromo group Chemical group Br* 0.000 description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
125000004429 atom Chemical group 0.000 description 8
229960004198 guanidine Drugs 0.000 description 8
229960000789 guanidine hydrochloride Drugs 0.000 description 8
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
239000000155 melt Substances 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 7
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
YSJNSSANBISNQN-UHFFFAOYSA-N 3-amino-5,6-dichloropyrazine-2-carbonitrile Chemical compound NC1=NC(Cl)=C(Cl)N=C1C#N YSJNSSANBISNQN-UHFFFAOYSA-N 0.000 description 6
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 6
238000001816 cooling Methods 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 5
JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OKSPUZDERJZNPO-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carbonitrile Chemical compound NC1=NC=C(Cl)N=C1C#N OKSPUZDERJZNPO-UHFFFAOYSA-N 0.000 description 3
WUAWAZWIWVBBEM-UHFFFAOYSA-N 3-amino-6-iodopyrazine-2-carbonitrile Chemical compound NC1=NC=C(I)N=C1C#N WUAWAZWIWVBBEM-UHFFFAOYSA-N 0.000 description 3
SDLFAEGTVBPHBK-UHFFFAOYSA-N 3-chloropyrazine-2-carbonitrile Chemical compound ClC1=NC=CN=C1C#N SDLFAEGTVBPHBK-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
DBPRLIBYSBDJSQ-UHFFFAOYSA-N NC=1C(=NC(=C[N+]1[O-])Br)C(=O)OC Chemical compound NC=1C(=NC(=C[N+]1[O-])Br)C(=O)OC DBPRLIBYSBDJSQ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
CITCTUNIFJOTHI-UHFFFAOYSA-N pteridine-2,4-diamine Chemical class N1=CC=NC2=NC(N)=NC(N)=C21 CITCTUNIFJOTHI-UHFFFAOYSA-N 0.000 description 3
AQENTCJPUUSHCK-UHFFFAOYSA-N 3,5-diamino-6-chloropyrazine-2-carbonitrile Chemical compound NC1=NC(N)=C(C#N)N=C1Cl AQENTCJPUUSHCK-UHFFFAOYSA-N 0.000 description 2
YAUJFGUNNMAZQR-UHFFFAOYSA-N 3-amino-5,6-dichloropyrazine-2-carboxamide Chemical compound NC(=O)C1=NC(Cl)=C(Cl)N=C1N YAUJFGUNNMAZQR-UHFFFAOYSA-N 0.000 description 2
XXCFWGIRIFRPER-UHFFFAOYSA-N 3-amino-6-bromopyrazine-2-carbonitrile Chemical compound NC1=NC=C(Br)N=C1C#N XXCFWGIRIFRPER-UHFFFAOYSA-N 0.000 description 2
YRLKALFVUYUKGQ-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carboxamide Chemical compound NC(=O)C1=NC(Cl)=CN=C1N YRLKALFVUYUKGQ-UHFFFAOYSA-N 0.000 description 2
VZFPXMWIXHIFRG-UHFFFAOYSA-N 3-amino-6-iodo-5-methoxypyrazine-2-carbonitrile Chemical compound NC=1C(=NC(=C(N=1)OC)I)C#N VZFPXMWIXHIFRG-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
KPLAIJXIAMFQAY-UHFFFAOYSA-N 6-iodopteridine-2,4-diamine Chemical compound NC1=NC2=NC=C(N=C2C(=N1)N)I KPLAIJXIAMFQAY-UHFFFAOYSA-N 0.000 description 2
DRFVRDKTSGGWMH-UHFFFAOYSA-N 7-bromo-6-chloropteridine-2,4-diamine Chemical compound NC1=NC2=NC(=C(N=C2C(=N1)N)Cl)Br DRFVRDKTSGGWMH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
USYMCUGEGUFUBI-UHFFFAOYSA-N methyl 3-amino-5,6-dichloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(Cl)N=C1N USYMCUGEGUFUBI-UHFFFAOYSA-N 0.000 description 2
MEYTYCRWYBFDOW-UHFFFAOYSA-N methyl 3-amino-6-bromo-5-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(Cl)N=C1N MEYTYCRWYBFDOW-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000000894 saliuretic effect Effects 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
JISQBJRFTCXDEO-UHFFFAOYSA-N 2-chloropteridine Chemical compound N1=CC=NC2=NC(Cl)=NC=C21 JISQBJRFTCXDEO-UHFFFAOYSA-N 0.000 description 1
PJISLFCKHOHLLP-UHFFFAOYSA-N 2-diethoxyphosphorylsulfanyl-n,n-diethylethanamine Chemical compound CCOP(=O)(OCC)SCCN(CC)CC PJISLFCKHOHLLP-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
SDTCGHLDTSGIRR-UHFFFAOYSA-N 3,5-dichloropyrazine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C(Cl)=N1 SDTCGHLDTSGIRR-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
AKECHHUMANPOQX-UHFFFAOYSA-N 3-(bromomethyl)-6,7-dichloro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CC(CBr)OC2=C1C=C(Cl)C(Cl)=C2 AKECHHUMANPOQX-UHFFFAOYSA-N 0.000 description 1
UTYGKDQHZGXWSM-UHFFFAOYSA-N 3-amino-5-bromo-6-chloropyrazine-2-carbonitrile Chemical compound NC1=NC(Br)=C(Cl)N=C1C#N UTYGKDQHZGXWSM-UHFFFAOYSA-N 0.000 description 1
OLQYDUAWXZYCHI-UHFFFAOYSA-N 3-amino-5-methoxypyrazine-2-carbonitrile Chemical compound COC1=CN=C(C#N)C(N)=N1 OLQYDUAWXZYCHI-UHFFFAOYSA-N 0.000 description 1
DQZMLNPFOOWBNS-UHFFFAOYSA-N 3-amino-6-bromo-5-chloropyrazine-2-carbonitrile Chemical compound NC1=NC(Cl)=C(Br)N=C1C#N DQZMLNPFOOWBNS-UHFFFAOYSA-N 0.000 description 1
QGZALVTXCYVWAN-UHFFFAOYSA-N 3-amino-6-bromo-5-methylpyrazine-2-carbonitrile Chemical compound CC1=NC(N)=C(C#N)N=C1Br QGZALVTXCYVWAN-UHFFFAOYSA-N 0.000 description 1
LPRKSJJRAPXPHU-UHFFFAOYSA-N 3-amino-6-bromo-5-methylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N1)C)Br)C(=O)N LPRKSJJRAPXPHU-UHFFFAOYSA-N 0.000 description 1
SGYHVFJRAIGOOE-UHFFFAOYSA-N 3-amino-6-bromo-5-phenylpyrazine-2-carbonitrile Chemical compound NC=1C(=NC(=C(N1)C1=CC=CC=C1)Br)C#N SGYHVFJRAIGOOE-UHFFFAOYSA-N 0.000 description 1
WPFHWWXSCLGOJS-UHFFFAOYSA-N 3-amino-6-bromo-5-phenylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N1)C1=CC=CC=C1)Br)C(=O)N WPFHWWXSCLGOJS-UHFFFAOYSA-N 0.000 description 1
LXCTZDCGLAEURA-UHFFFAOYSA-N 3-amino-6-chloro-5-methoxypyrazine-2-carbonitrile Chemical compound NC=1C(=NC(=C(N1)OC)Cl)C#N LXCTZDCGLAEURA-UHFFFAOYSA-N 0.000 description 1
SZMCILPTSHSVRP-UHFFFAOYSA-N 3-amino-6-chloro-5-methylsulfanylpyrazine-2-carbonitrile Chemical compound CSC1=NC(N)=C(C#N)N=C1Cl SZMCILPTSHSVRP-UHFFFAOYSA-N 0.000 description 1
QDHZJXAAFQGWIY-UHFFFAOYSA-N 3-amino-6-iodopyrazine-2-carboxamide Chemical compound NC(=O)C1=NC(I)=CN=C1N QDHZJXAAFQGWIY-UHFFFAOYSA-N 0.000 description 1
GPIZLEHIVRHDAW-UHFFFAOYSA-N 3-aminopyrazine-2-carbonitrile Chemical compound NC1=NC=CN=C1C#N GPIZLEHIVRHDAW-UHFFFAOYSA-N 0.000 description 1
NAPIQNUAYLKBHM-UHFFFAOYSA-N 3-bromopyrazine-2-carbonitrile Chemical compound BrC1=NC=CN=C1C#N NAPIQNUAYLKBHM-UHFFFAOYSA-N 0.000 description 1
LPQDBXNKRAKTHX-UHFFFAOYSA-N 3-iodopyrazine-2-carbonitrile Chemical compound IC1=NC=CN=C1C#N LPQDBXNKRAKTHX-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
CLWIERBYKHFBAA-UHFFFAOYSA-N 6-bromo-7-methylpteridine-2,4-diamine Chemical compound NC1=NC(N)=C2N=C(Br)C(C)=NC2=N1 CLWIERBYKHFBAA-UHFFFAOYSA-N 0.000 description 1
QSJNGXHBZFZDIL-UHFFFAOYSA-N 6-bromo-7-phenylpteridine-2,4-diamine Chemical compound NC1=NC2=NC(=C(N=C2C(=N1)N)Br)C1=CC=CC=C1 QSJNGXHBZFZDIL-UHFFFAOYSA-N 0.000 description 1
JBCMGPUGHFLRJT-UHFFFAOYSA-N 6-bromopteridine-2,4-diamine Chemical compound N1=C(Br)C=NC2=NC(N)=NC(N)=C21 JBCMGPUGHFLRJT-UHFFFAOYSA-N 0.000 description 1
SNWNPIIBXQRXGH-UHFFFAOYSA-N 6-chloropteridine-2,4,7-triamine Chemical compound N1=C(Cl)C(N)=NC2=NC(N)=NC(N)=C21 SNWNPIIBXQRXGH-UHFFFAOYSA-N 0.000 description 1
OTYIEMDMJHKNBP-UHFFFAOYSA-N 6-chloropteridine-2,4-diamine Chemical compound N1=C(Cl)C=NC2=NC(N)=NC(N)=C21 OTYIEMDMJHKNBP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
QNRXPVUHIBZHBW-UHFFFAOYSA-N NC1=NC2=NC(=C(N=C2C(=N1)N)I)OC Chemical compound NC1=NC2=NC(=C(N=C2C(=N1)N)I)OC QNRXPVUHIBZHBW-UHFFFAOYSA-N 0.000 description 1
LZRVEGUFVUPAJH-UHFFFAOYSA-N NC=1C(=NC(=C[N+]1[O-])Cl)C(=O)OC Chemical compound NC=1C(=NC(=C[N+]1[O-])Cl)C(=O)OC LZRVEGUFVUPAJH-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
YPNWGLNCDBBKNX-UHFFFAOYSA-N carbamimidoyl bromide Chemical compound NC(Br)=N YPNWGLNCDBBKNX-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
GXNWVJBKCSDFIL-UHFFFAOYSA-N methyl 3-amino-6-bromo-5-methylpyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(C)N=C1N GXNWVJBKCSDFIL-UHFFFAOYSA-N 0.000 description 1
XANOMKZNTWJRBS-UHFFFAOYSA-N methyl 3-amino-6-bromo-5-phenylpyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N1)C1=CC=CC=C1)Br)C(=O)OC XANOMKZNTWJRBS-UHFFFAOYSA-N 0.000 description 1
CNXSIRHOIFRMOB-UHFFFAOYSA-N methyl 3-amino-6-bromopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=CN=C1N CNXSIRHOIFRMOB-UHFFFAOYSA-N 0.000 description 1
FDLARAKNPMCCKJ-UHFFFAOYSA-N methyl 3-amino-6-iodopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(I)=CN=C1N FDLARAKNPMCCKJ-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DDDZNRSTGCSUJP-UHFFFAOYSA-N n'-(3-cyano-5-iodopyrazin-2-yl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC=C(I)N=C1C#N DDDZNRSTGCSUJP-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
150000003195 pteridines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL2657866A 1965-10-04 1966-09-26 Pethridine compounds and their preparation IL26578A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49289865A	1965-10-04	1965-10-04

Publications (1)

Publication Number	Publication Date
IL26578A true IL26578A (en)	1970-11-30

Family

ID=23958060

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2657866A IL26578A (en)	1965-10-04	1966-09-26	Pethridine compounds and their preparation

Country Status (9)

Country	Link
BE (1)	BE687730A (fr)
BR (1)	BR6683209D0 (fr)
CH (1)	CH479601A (fr)
DE (1)	DE1620034A1 (fr)
ES (1)	ES332322A1 (fr)
FR (1)	FR6028M (fr)
GB (1)	GB1149640A (fr)
IL (1)	IL26578A (fr)
NL (1)	NL6613936A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2005231507B2 (en)	2004-04-08	2012-03-01	Targegen, Inc.	Benzotriazine inhibitors of kinases
NZ588896A (en)	2004-08-25	2012-05-25	Targegen Inc	Heterocyclic compounds and methods of use
WO2007127366A2 (fr)	2006-04-25	2007-11-08	Targegen, Inc.	Inhibiteurs de kinases et leurs procédés d'utilisation

1966
- 1966-09-26 IL IL2657866A patent/IL26578A/en unknown
- 1966-09-27 BR BR18320966A patent/BR6683209D0/pt unknown
- 1966-09-28 GB GB4340166A patent/GB1149640A/en not_active Expired
- 1966-09-28 CH CH1397766A patent/CH479601A/de not_active IP Right Cessation
- 1966-09-29 ES ES0332322A patent/ES332322A1/es not_active Expired
- 1966-10-03 DE DE19661620034 patent/DE1620034A1/de active Pending
- 1966-10-03 NL NL6613936A patent/NL6613936A/xx unknown
- 1966-10-03 BE BE687730D patent/BE687730A/xx unknown
- 1966-12-23 FR FR88769A patent/FR6028M/fr not_active Expired

Also Published As

Publication number	Publication date
FR6028M (fr)	1968-05-13
ES332322A1 (es)	1967-07-16
CH479601A (de)	1969-10-15
BR6683209D0 (pt)	1973-12-26
GB1149640A (en)	1969-04-23
BE687730A (fr)	1967-04-03
NL6613936A (fr)	1967-04-05
DE1620034A1 (de)	1970-02-05

Publication	Publication Date	Title
EP0260817B1 (fr)	1991-05-15	Quinazolinediones et pyridopyrimidinediones
NO151320B (no)	1984-12-10	Analogifremgangsmaate for fremstilling av terapeutisk aktiv pyrrolidylmetyl-2-metoksy-4-amino-5-isopropyl-sulfonylbenzamider
US3487082A (en)	1969-12-30	2,4 - diamino - 6 - halopteridines and processes for their preparation
EP0104522B1 (fr)	1991-05-29	Dérivés de la pyrazolo(3,4-b)pyridine et leur procédé de préparation
HU197749B (en)	1989-05-29	Process for producing /3,4-d/pyrimidine derivatives and pharmaceutical compositions comprising these compounds as active ingredient
DE69629341T2 (de)	2004-06-09	Pyrrolocarbazolderivate
NO146096B (no)	1982-04-19	Analogifremgangsmaate ved fremstilling av thienothiazinderivater
HU178593B (en)	1982-05-28	Process for producing 3-hydroxy-6-phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocine derivatives
US3635978A (en)	1972-01-18	Amino pyrimidines
NO764039L (fr)	1977-06-06
NO158739B (no)	1988-07-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-piperazinopyrimidinderivater.
JPH0351704B2 (fr)	1991-08-07
FI84720C (fi)	1992-01-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrido/2,3-d/pyrimidin-2,4-dionderivat.
NO166712B (no)	1991-05-21	Fremgangsmaate ved fremstilling av pyrrolidonderivater.
US4261997A (en)	1981-04-14	4-Alkyl-pyrazolo[5,1-b]-quinazolin-9(4H)-ones and anti-allergic compositions containing them
US4608375A (en)	1986-08-26	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
US4625028A (en)	1986-11-25	6-aryluracils and selected novel intermediates used in the preparation thereof
US3751412A (en)	1973-08-07	2-amino-1,5-benzodiazocine derivatives
NO751594L (fr)	1976-01-06
NO170542B (no)	1992-07-20	Fremgangsmaate for fremstilling av en basisk thioether og saltet derav
Habib et al.	1984	Ylides of heterocycles. VII.. I‐, N‐, P‐and S‐ylides of pyrimidones
Wawzonek et al.	1971	Pyrolysis of 1-methyl-2-phenylpiperidine-1-acylimides
NO784094L (no)	1979-06-15	3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling
US4521599A (en)	1985-06-04	Process for the preparation of 1,3-oxazine-4-ones
US4593030A (en)	1986-06-03	Use of 6-aryluracils as antiinflammatory and antiarthritic agents