GB2219999A - Substituted 5-pyrimidinecarboxamides and treatment of leukemia - Google Patents
Substituted 5-pyrimidinecarboxamides and treatment of leukemia Download PDFInfo
- Publication number
- GB2219999A GB2219999A GB8815055A GB8815055A GB2219999A GB 2219999 A GB2219999 A GB 2219999A GB 8815055 A GB8815055 A GB 8815055A GB 8815055 A GB8815055 A GB 8815055A GB 2219999 A GB2219999 A GB 2219999A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidinecarboxamide
- oxo
- hydroxy
- tetrahydro
- dihydro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 208000032839 leukemia Diseases 0.000 title claims abstract description 21
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical class NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 45
- UMYLUVCVHHSAQH-UHFFFAOYSA-N N-(2-fluorophenyl)-4-hydroxy-6-oxo-1H-pyrimidine-5-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)C=1C(NC=NC1O)=O UMYLUVCVHHSAQH-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- LDRKHQOYFHSVGZ-UHFFFAOYSA-N 4-hydroxy-6-oxo-n-phenyl-1h-pyrimidine-5-carboxamide Chemical compound N1=CNC(=O)C(C(=O)NC=2C=CC=CC=2)=C1O LDRKHQOYFHSVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- OIPGJYLTAWKCEU-UHFFFAOYSA-N n-(4-fluorophenyl)-4-hydroxy-6-oxo-2,3-dihydro-1h-pyrimidine-5-carboxamide Chemical compound O=C1NCNC(O)=C1C(=O)NC1=CC=C(F)C=C1 OIPGJYLTAWKCEU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000003843 furanosyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003132 pyranosyl group Chemical group 0.000 claims description 3
- UENSFNQLJXEEFO-UHFFFAOYSA-N N-(2-fluorophenyl)-4-hydroxy-6-oxo-2,3-dihydro-1H-pyrimidine-5-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)C=1C(NCNC1O)=O UENSFNQLJXEEFO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BMTOUTOMCXXGRE-UHFFFAOYSA-N 4-hydroxy-6-oxo-n-phenyl-2,3-dihydro-1h-pyrimidine-5-carboxamide Chemical compound O=C1NCNC(O)=C1C(=O)NC1=CC=CC=C1 BMTOUTOMCXXGRE-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- BWSOSTPVYAGLPG-UHFFFAOYSA-N n-(4-fluorophenyl)-4-hydroxy-6-oxo-1h-pyrimidine-5-carboxamide Chemical compound N1=CNC(=O)C(C(=O)NC=2C=CC(F)=CC=2)=C1O BWSOSTPVYAGLPG-UHFFFAOYSA-N 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 abstract description 5
- 230000004614 tumor growth Effects 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 47
- 230000000694 effects Effects 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- 230000000719 anti-leukaemic effect Effects 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 201000011510 cancer Diseases 0.000 description 8
- 238000005303 weighing Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000007868 Raney catalyst Substances 0.000 description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- -1 arabinopyranosyl Chemical group 0.000 description 6
- 238000002512 chemotherapy Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000001207 fluorophenyl group Chemical group 0.000 description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 210000003567 ascitic fluid Anatomy 0.000 description 3
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- 230000004083 survival effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000011765 DBA/2 mouse Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
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- 239000003429 antifungal agent Substances 0.000 description 2
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- 239000002246 antineoplastic agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NGAIRFWHCKPVHH-UHFFFAOYSA-N n-(2-fluorophenyl)pyrimidine-5-carboxamide Chemical class FC1=CC=CC=C1NC(=O)C1=CN=CN=C1 NGAIRFWHCKPVHH-UHFFFAOYSA-N 0.000 description 2
- 239000002777 nucleoside Chemical class 0.000 description 2
- 125000003835 nucleoside group Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HZJBBHSANAZJIM-UHFFFAOYSA-N 2-(2-fluorophenyl)pyrimidine-5-carboxamide Chemical class N1=CC(C(=O)N)=CN=C1C1=CC=CC=C1F HZJBBHSANAZJIM-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ORXNJGMITSNRKH-UHFFFAOYSA-N 2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical class NC(=O)C=1C=NC(=S)NC=1 ORXNJGMITSNRKH-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- LPSKSLRGCHZEDL-UHFFFAOYSA-N CC(CC1)CCC1C=C Chemical compound CC(CC1)CCC1C=C LPSKSLRGCHZEDL-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
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- 239000007972 injectable composition Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JSOKTPGOKUPVOW-UHFFFAOYSA-N n-(2-fluorophenyl)-6-hydroxy-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(=O)C(C(=O)NC=2C(=CC=CC=2)F)=C1O JSOKTPGOKUPVOW-UHFFFAOYSA-N 0.000 description 1
- UKGRGRZTNHOIGU-UHFFFAOYSA-N n-(4-fluorophenyl)-6-hydroxy-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(=O)C(C(=O)NC=2C=CC(F)=CC=2)=C1O UKGRGRZTNHOIGU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 230000007170 pathology Effects 0.000 description 1
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- 229960003742 phenol Drugs 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE8800818A BE1001263A4 (fr) | 1988-07-14 | 1988-07-14 | Procede en vue de provoquer la regression de la leucemie et l'inhibition de la croissance des tumeurs chez les mammiferes. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8815055D0 GB8815055D0 (en) | 1988-08-03 |
| GB2219999A true GB2219999A (en) | 1989-12-28 |
Family
ID=3883532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8815055A Withdrawn GB2219999A (en) | 1988-07-14 | 1988-06-24 | Substituted 5-pyrimidinecarboxamides and treatment of leukemia |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE1001263A4 (enrdf_load_stackoverflow) |
| FR (1) | FR2628869A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2219999A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2174391A (en) * | 1985-04-22 | 1986-11-05 | Uniroyal Chem Co Inc | 5-pyrimidinecarboxamides and treatment of leukemia and tumours therewith |
-
1988
- 1988-03-17 FR FR8803462A patent/FR2628869A1/fr active Pending
- 1988-06-24 GB GB8815055A patent/GB2219999A/en not_active Withdrawn
- 1988-07-14 BE BE8800818A patent/BE1001263A4/fr not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2174391A (en) * | 1985-04-22 | 1986-11-05 | Uniroyal Chem Co Inc | 5-pyrimidinecarboxamides and treatment of leukemia and tumours therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8815055D0 (en) | 1988-08-03 |
| FR2628869A1 (enrdf_load_stackoverflow) | 1989-09-22 |
| BE1001263A4 (fr) | 1989-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |