NO823075L - Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater - Google Patents

Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater

Info

Publication number: NO823075L
Authority: NO; Norway
Prior art keywords: group; formula; compound; alkyl; halogen
Prior art date: 1981-09-11

Application number

NO823075A

Other languages

English (en)

Norwegian (no)

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.)

1981-09-11

Filing date

1982-09-10

Publication date

1983-03-14

1982-09-10 Application filed by Nyegaard & Co As filed Critical Nyegaard & Co As

1983-03-14 Publication of NO823075L publication Critical patent/NO823075L/no

Links

238000000034 method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 52
150000003839 salts Chemical class 0.000 claims abstract description 20
125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
-1 hydroxy, mercapto Chemical class 0.000 claims abstract description 16
230000002159 abnormal effect Effects 0.000 claims abstract description 14
125000003118 aryl group Chemical group 0.000 claims abstract description 14
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
230000002378 acidificating effect Effects 0.000 claims abstract description 7
125000004122 cyclic group Chemical group 0.000 claims abstract description 7
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
NEFLUDBQLHZUBN-UHFFFAOYSA-N 5-chloro-n-methyl-2-oxopyrimidine-1-carboxamide Chemical compound CNC(=O)N1C=C(Cl)C=NC1=O NEFLUDBQLHZUBN-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
230000010261 cell growth Effects 0.000 claims description 3
VQZIDYBSUQELDS-UHFFFAOYSA-N 5-bromo-n-methyl-2-oxopyrimidine-1-carboxamide Chemical compound CNC(=O)N1C=C(Br)C=NC1=O VQZIDYBSUQELDS-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 15
230000004663 cell proliferation Effects 0.000 abstract description 6
KUAWDIFZEBBSPW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrimidin-2-one Chemical compound OC1=NC=C(C(F)(F)F)C=N1 KUAWDIFZEBBSPW-UHFFFAOYSA-N 0.000 abstract description 4
125000002015 acyclic group Chemical group 0.000 abstract description 4
239000012948 isocyanate Substances 0.000 abstract description 2
150000002513 isocyanates Chemical class 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
210000004027 cell Anatomy 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
VTUDATOSQGYWML-UHFFFAOYSA-N 5-bromo-1h-pyrimidin-2-one Chemical compound OC1=NC=C(Br)C=N1 VTUDATOSQGYWML-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000001624 naphthyl group Chemical group 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000022131 cell cycle Effects 0.000 description 3
230000032823 cell division 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
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003457 sulfones Chemical class 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
OCSYCDVQABSEPJ-UHFFFAOYSA-N 5-chloro-1h-pyrimidin-2-one Chemical compound OC1=NC=C(Cl)C=N1 OCSYCDVQABSEPJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
239000012038 nucleophile Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical class 0.000 description 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
OAXSVEFCBLZGCA-UHFFFAOYSA-N 1-chloro-4-(isocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=O)C=C1 OAXSVEFCBLZGCA-UHFFFAOYSA-N 0.000 description 1
QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 1
CDDYYRHLZPJLPD-UHFFFAOYSA-N 2-(isocyanatomethyl)thiophene Chemical compound O=C=NCC1=CC=CS1 CDDYYRHLZPJLPD-UHFFFAOYSA-N 0.000 description 1
TYCYTQLXAIDJNF-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CN=C(Cl)N=C1 TYCYTQLXAIDJNF-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
SHVVSKCXWMEDRW-UHFFFAOYSA-N 3-isocyanatopyridine Chemical compound O=C=NC1=CC=CN=C1 SHVVSKCXWMEDRW-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
UVUURONBAGKRDB-UHFFFAOYSA-N 5-bromo-2-oxo-n-phenylpyrimidine-1-carboxamide Chemical compound C1=C(Br)C=NC(=O)N1C(=O)NC1=CC=CC=C1 UVUURONBAGKRDB-UHFFFAOYSA-N 0.000 description 1
GUMDCHRESWCROZ-UHFFFAOYSA-N 5-bromo-n-naphthalen-1-yl-2-oxopyrimidine-1-carboxamide Chemical compound C1=C(Br)C=NC(=O)N1C(=O)NC1=CC=CC2=CC=CC=C12 GUMDCHRESWCROZ-UHFFFAOYSA-N 0.000 description 1
HPABFFGQPLJKBP-UHFFFAOYSA-N 5-fluoro-1H-pyrimidin-2-one Chemical compound OC1=NC=C(F)C=N1 HPABFFGQPLJKBP-UHFFFAOYSA-N 0.000 description 1
DSFIUOVISGTSTA-UHFFFAOYSA-N 5-fluoro-n-methyl-2-oxopyrimidine-1-carboxamide Chemical compound CNC(=O)N1C=C(F)C=NC1=O DSFIUOVISGTSTA-UHFFFAOYSA-N 0.000 description 1
PVHCYDBPRLPQMP-UHFFFAOYSA-N 5-iodo-1h-pyrimidin-2-one Chemical compound OC1=NC=C(I)C=N1 PVHCYDBPRLPQMP-UHFFFAOYSA-N 0.000 description 1
FYYQLYKYJRDICC-UHFFFAOYSA-N 5-iodo-n-methyl-2-oxopyrimidine-1-carboxamide Chemical compound CNC(=O)N1C=C(I)C=NC1=O FYYQLYKYJRDICC-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
244000215068 Acacia senegal Species 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
230000006820 DNA synthesis Effects 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
230000018199 S phase Effects 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000000837 carbohydrate group Chemical group 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000037406 food intake Effects 0.000 description 1
125000003843 furanosyl group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
125000003147 glycosyl group Chemical group 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000016507 interphase Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
208000032839 leukemia Diseases 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
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000031864 metaphase Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
UFEUKIVPSCKBES-UHFFFAOYSA-N n-naphthalen-1-yl-2-oxo-5-(trifluoromethyl)pyrimidine-1-carboxamide Chemical compound C1=C(C(F)(F)F)C=NC(=O)N1C(=O)NC1=CC=CC2=CC=CC=C12 UFEUKIVPSCKBES-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-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
150000007530 organic bases Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000003132 pyranosyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
125000001302 tertiary amino group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 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
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
Epidemiology (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)
Pyrrole Compounds (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)

NO823075A 1981-09-11 1982-09-10 Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater NO823075L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8127505		1981-09-11

Publications (1)

Publication Number	Publication Date
NO823075L true NO823075L (no)	1983-03-14

Family

ID=10524445

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO823075A NO823075L (no)	1981-09-11	1982-09-10	Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater

Country Status (11)

Country	Link
US (1)	US4478839A (da)
EP (1)	EP0074820B1 (da)
JP (1)	JPS5857368A (da)
AT (1)	ATE21693T1 (da)
AU (1)	AU8818882A (da)
DE (1)	DE3272892D1 (da)
DK (1)	DK404982A (da)
ES (1)	ES515640A0 (da)
NO (1)	NO823075L (da)
NZ (1)	NZ201883A (da)
ZA (1)	ZA826660B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK83783A (da) *	1982-02-24	1983-08-25	Nyegaard & Co As	Fremgangsmaade til fremstilling af substituerede pyrimidin-2-oner
JPH0613535B2 (ja) *	1984-09-10	1994-02-23	株式会社三和化学研究所	新規な有機珪素化合物、その製法並びに該化合物を有効成分とする抗腫瘍剤
US4675321A (en) *	1986-02-07	1987-06-23	Merck & Co., Inc.	Substituted pyrimidines useful as calcium channel blockers
JP2873340B2 (ja) *	1988-04-29	1999-03-24	武田薬品工業株式会社	抗生物質ｔａｎ―１０５７，その製造法および用途
US8679231B2 (en)	2011-01-19	2014-03-25	Advanced Technology Materials, Inc.	PVDF pyrolyzate adsorbent and gas storage and dispensing system utilizing same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1561290A (en) *	1975-10-16	1980-02-20	Nyegaard & Co As	Pyrimid - 2 - ones
US4052400A (en) *	1976-10-29	1977-10-04	Morton-Norwich Products, Inc.	Hypertensive 1-substituted 2(1h)-pyrimidones

1982
- 1982-09-10 DK DK404982A patent/DK404982A/da not_active Application Discontinuation
- 1982-09-10 NO NO823075A patent/NO823075L/no unknown
- 1982-09-10 NZ NZ201883A patent/NZ201883A/en unknown
- 1982-09-10 AT AT82304780T patent/ATE21693T1/de active
- 1982-09-10 EP EP82304780A patent/EP0074820B1/en not_active Expired
- 1982-09-10 ES ES515640A patent/ES515640A0/es active Granted
- 1982-09-10 AU AU88188/82A patent/AU8818882A/en not_active Abandoned
- 1982-09-10 DE DE8282304780T patent/DE3272892D1/de not_active Expired
- 1982-09-10 ZA ZA826660A patent/ZA826660B/xx unknown
- 1982-09-10 US US06/416,670 patent/US4478839A/en not_active Expired - Fee Related
- 1982-09-10 JP JP57156882A patent/JPS5857368A/ja active Pending

Also Published As

Publication number	Publication date
DE3272892D1 (en)	1986-10-02
NZ201883A (en)	1985-11-08
JPS5857368A (ja)	1983-04-05
DK404982A (da)	1983-03-12
ES8308860A1 (es)	1983-10-01
AU8818882A (en)	1983-03-17
ATE21693T1 (de)	1986-09-15
EP0074820A1 (en)	1983-03-23
ZA826660B (en)	1983-08-31
US4478839A (en)	1984-10-23
EP0074820B1 (en)	1986-08-27
ES515640A0 (es)	1983-10-01

Publication	Publication Date	Title
JP5341763B2 (ja)	2013-11-13	２−アミノカルボニル−ピリジン誘導体
NO810064L (no)	1981-07-13	Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav
RU2022963C1 (ru)	1994-11-15	1,3-замещенные сульфонилмочевины или их фармацевтически приемлемые соли, обладающие противоопухолевой активностью
EA013371B1 (ru)	2010-04-30	Новые соединения, содержащие их фармацевтические композиции и способы их применения
JPH10508881A (ja)	1998-09-02	縮合した１，２，４−チアジアジン及び縮合した１，４−チアジン誘導体、これらの製造および使用
NO160781B (no)	1989-02-20	1,2,5-tiadiazolderivater.
EP0017152A1 (en)	1980-10-15	Novel heterocyclic substituted pyrazinoylguanidines, processes for preparing and a pharmaceutical composition containing the same
JPH10330355A (ja)	1998-12-15	芳香族ジセレニド及びセレノスルフィド、それらの製造法及び使用、新規治療での使用
NO823075L (no)	1983-03-14	Fremgangsmaate for fremstilling av substituerte pyrimid-2-on-derivater
NO163692B (no)	1990-03-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive oksazafosforin-4-tio-alkansulfonsyrer og salter derav.
NO120758B (da)	1970-11-30
NO160514B (no)	1989-01-16	Analogifremgangsm te for fremstilling av farmasoeytisk aktive pyrimid-2-on-derivater.
US3635946A (en)	1972-01-18	N1-(2'-furanidyl)-derivatives of 5-substituted uracils
EP2058306A1 (en)	2009-05-13	Heteroaryl-substituted 2-pyridinyl-methylamine derivatives
Bosin et al.	1973	Routes of functionalized guanidines. Synthesis of guanidino diesters
CA1336516C (en)	1995-08-01	Acyl derivatives of 2-amino-4-substituted-5-hydroxy pyrimidines
US3818033A (en)	1974-06-18	5(4)-amino-substituted imidazoles
JPS5842195B2 (ja)	1983-09-17	チアゾロイソキノリン誘導体の製法
Vas’ Kevich et al.	2006	Synthesis of amino derivatives of triazolopyrimidine
NO161440B (no)	1989-05-08	Analogifremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-oner.
CA1138866A (en)	1983-01-04	Chemical process for preparing isoxazolo-benzoxazinone derivatives
NO811977L (no)	1981-12-14	Imidazobenzotiadiazepiner, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser, samt deres terapeutiske anvendelse
SU503522A3 (ru)	1976-02-15	Способ получени карбаматных производных 2,4-диоксиметилтиазола
US3929789A (en)	1975-12-30	Pyrimidinyl acetic acid derivatives and processes for their production
Larsen et al.	2001	Synthesis and anti‐HIV activity of HEPT and S‐DABO‐analogues with 5‐Benzyl and 5‐Phenyl substituents