CA2071000A1 - 2,4,6-triaminopyrimidines oxygenees en 5 - Google Patents

2,4,6-triaminopyrimidines oxygenees en 5

Info

Publication number: CA2071000A1
Authority: CA; Canada
Prior art keywords: alkyl; pyrimidine; alpha; pyrrolidinyl; beta
Prior art date: 1990-01-26
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.): Abandoned

Application number

CA002071000A

Other languages

English (en)

Inventor

John M. Mccall

Eric J. Jacobsen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Individual

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.)

1990-01-26

Filing date

1991-01-08

Publication date

1991-07-27

1991-01-08 Application filed by Individual filed Critical Individual

1991-07-27 Publication of CA2071000A1 publication Critical patent/CA2071000A1/fr

Status Abandoned legal-status Critical Current

Links

-1 amino substituted pyrimidines Chemical class 0.000 claims abstract description 139
150000003230 pyrimidines Chemical class 0.000 claims abstract description 103
GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical group O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims abstract description 14
150000003431 steroids Chemical group 0.000 claims abstract description 12
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 77
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 59
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
125000004193 piperazinyl group Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 16
ZBORFALATDILQW-UHFFFAOYSA-N tert-butyl 4-(5-hydroxy-2,6-dipyrrolidin-1-ylpyrimidin-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC(N2CCCC2)=NC(N2CCCC2)=C1O ZBORFALATDILQW-UHFFFAOYSA-N 0.000 claims description 15
LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
230000015572 biosynthetic process Effects 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
XXSYYKLEYGBWDV-UHFFFAOYSA-N 4-piperazin-1-yl-2,6-dipyrrolidin-1-ylpyrimidin-5-ol Chemical compound OC1=C(N2CCCC2)N=C(N2CCCC2)N=C1N1CCNCC1 XXSYYKLEYGBWDV-UHFFFAOYSA-N 0.000 claims description 10
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000005322 morpholin-1-yl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229940002612 prodrug Drugs 0.000 claims description 4
239000000651 prodrug Substances 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
GDYGZVXXCYUYTH-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-2,6-dipyrrolidin-1-ylpyrimidin-5-ol Chemical compound OC=1C(=NC(=NC=1N1CCCC1)N1CCCC1)N1CCN(CC1)C GDYGZVXXCYUYTH-UHFFFAOYSA-N 0.000 claims description 2
CFFANFFYDMKOBZ-UHFFFAOYSA-N 4-(4-propylpiperazin-1-yl)-2,6-dipyrrolidin-1-ylpyrimidin-5-ol Chemical compound OC=1C(=NC(=NC=1N1CCCC1)N1CCCC1)N1CCN(CC1)CCC CFFANFFYDMKOBZ-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
235000000346 sugar Nutrition 0.000 claims description 2
125000005208 trialkylammonium group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 36
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 34
229940050390 benzoate Drugs 0.000 claims 8
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 5
LKDRXBCSQODPBY-VRPWFDPXSA-N D-fructopyranose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-VRPWFDPXSA-N 0.000 claims 4
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
125000002345 steroid group Chemical group 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229920000136 polysorbate Polymers 0.000 claims 1
206010019196 Head injury Diseases 0.000 abstract description 8
239000000543 intermediate Substances 0.000 abstract description 2
208000006011 Stroke Diseases 0.000 abstract 1
208000020431 spinal cord injury Diseases 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 47
229940073584 methylene chloride Drugs 0.000 description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
229910052799 carbon Inorganic materials 0.000 description 36
125000001424 substituent group Chemical group 0.000 description 31
229940093499 ethyl acetate Drugs 0.000 description 27
235000019439 ethyl acetate Nutrition 0.000 description 27
229910052943 magnesium sulfate Inorganic materials 0.000 description 24
235000019341 magnesium sulphate Nutrition 0.000 description 24
229910052739 hydrogen Inorganic materials 0.000 description 22
238000000034 method Methods 0.000 description 22
238000010626 work up procedure Methods 0.000 description 22
238000003818 flash chromatography Methods 0.000 description 19
238000000746 purification Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 16
150000001721 carbon Chemical group 0.000 description 14
238000011282 treatment Methods 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
239000000126 substance Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
208000014674 injury Diseases 0.000 description 9
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000001356 surgical procedure Methods 0.000 description 9
230000008733 trauma Effects 0.000 description 9
230000006378 damage Effects 0.000 description 8
239000003814 drug Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
229940022663 acetate Drugs 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
238000003556 assay Methods 0.000 description 7
229940079593 drug Drugs 0.000 description 7
238000010265 fast atom bombardment Methods 0.000 description 7
OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
239000003862 glucocorticoid Substances 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
206010020751 Hypersensitivity Diseases 0.000 description 5
208000012902 Nervous system disease Diseases 0.000 description 5
208000025966 Neurological disease Diseases 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
230000003412 degenerative effect Effects 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
206010040070 Septic Shock Diseases 0.000 description 4
206010042220 Stress ulcer Diseases 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
208000025865 Ulcer Diseases 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 4
208000000718 duodenal ulcer Diseases 0.000 description 4
230000003859 lipid peroxidation Effects 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
230000028327 secretion Effects 0.000 description 4
208000011580 syndromic disease Diseases 0.000 description 4
229940037128 systemic glucocorticoids Drugs 0.000 description 4
NSRDEWWYYPYECY-UHFFFAOYSA-N tert-butyl 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC(N2CCCC2)=NC(N2CCCC2)=N1 NSRDEWWYYPYECY-UHFFFAOYSA-N 0.000 description 4
231100000397 ulcer Toxicity 0.000 description 4
MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
239000004342 Benzoyl peroxide Substances 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
208000027089 Parkinsonian disease Diseases 0.000 description 3
206010034010 Parkinsonism Diseases 0.000 description 3
206010044541 Traumatic shock Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
229940009456 adriamycin Drugs 0.000 description 3
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
229910001870 ammonium persulfate Inorganic materials 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
238000002680 cardiopulmonary resuscitation Methods 0.000 description 3
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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230000036303 septic shock Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
230000004614 tumor growth Effects 0.000 description 3
ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
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208000032843 Hemorrhage Diseases 0.000 description 2
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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150000007513 acids Chemical class 0.000 description 2
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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150000002500 ions Chemical class 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
230000003637 steroidlike Effects 0.000 description 2
230000035882 stress Effects 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
230000009424 thromboembolic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000000472 traumatic effect Effects 0.000 description 2
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IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D239/50—Three nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CA002071000A 1990-01-26 1991-01-08 2,4,6-triaminopyrimidines oxygenees en 5 Abandoned CA2071000A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US47122890A	1990-01-26	1990-01-26
US471,228		1990-01-26

Publications (1)

Publication Number	Publication Date
CA2071000A1 true CA2071000A1 (fr)	1991-07-27

Family

ID=23870783

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002071000A Abandoned CA2071000A1 (fr)	1990-01-26	1991-01-08	2,4,6-triaminopyrimidines oxygenees en 5

Country Status (7)

Country	Link
EP (1)	EP0513177A1 (fr)
JP (1)	JPH05503705A (fr)
KR (1)	KR927003579A (fr)
AU (1)	AU642711B2 (fr)
CA (1)	CA2071000A1 (fr)
NZ (1)	NZ236801A (fr)
WO (1)	WO1991011453A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUT64323A (en) *	1992-06-09	1993-12-28	Richter Gedeon Vegyeszet	Process for production new piperazinyl-bis(alkyl-amino)-pyrimidine derivatives
HU209678B (en)	1992-06-09	1994-10-28	Richter Gedeon Vegyeszet	Process for producing biologically active eburnamenin-14-carbonyl-amino derivatives and pharmaceutical compositions containing them
HU212308B (en) *	1992-06-09	1996-05-28	Richter Gedeon Vegyeszet	Process for producing novel pregnane steroids and pharmaceutical compositions containing the same
DE4330727C2 (de) *	1993-09-10	1998-02-19	Jenapharm Gmbh	Steroidzwischenprodukte und Verfahren zu ihrer Herstellung
DE4338314C1 (de)	1993-11-10	1995-03-30	Jenapharm Gmbh	Pharmazeutische Präparate zur Prophylaxe und Therapie radikalvermittelter Zellschädigungen
DE4338316A1 (de) *	1993-11-10	1995-05-11	Jenapharm Gmbh	Neue Steroide mit radikophilen Substituenten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1987001706A2 (fr) *	1985-09-12	1987-03-26	The Upjohn Company	Amino-steroides c20 a c26
WO1987007895A1 (fr) *	1986-06-23	1987-12-30	The Upjohn Company	Aminoesters corticaux et du type androstane
CA1338012C (fr) *	1987-04-27	1996-01-30	John Michael Mccall	Amines possedant des proprietes pharmaceutiques
FR2644787B1 (fr) *	1989-03-22	1995-02-03	Roussel Uclaf	Nouveaux steroides 21 aminosubstitues, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant
FR2644789B1 (fr) *	1989-03-22	1995-02-03	Roussel Uclaf	Nouveaux steroides 19-nor, 3-ceto comportant une chaine en 17 aminosubstituee, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant

1991
- 1991-01-08 CA CA002071000A patent/CA2071000A1/fr not_active Abandoned
- 1991-01-08 KR KR1019920701769A patent/KR927003579A/ko not_active Withdrawn
- 1991-01-08 JP JP3504351A patent/JPH05503705A/ja active Pending
- 1991-01-08 WO PCT/US1991/000017 patent/WO1991011453A2/fr not_active Ceased
- 1991-01-08 AU AU72438/91A patent/AU642711B2/en not_active Ceased
- 1991-01-08 EP EP91904133A patent/EP0513177A1/fr not_active Withdrawn
- 1991-01-17 NZ NZ236801A patent/NZ236801A/en unknown

Also Published As

Publication number	Publication date
WO1991011453A3 (fr)	1991-11-14
EP0513177A1 (fr)	1992-11-19
JPH05503705A (ja)	1993-06-17
KR927003579A (ko)	1992-12-18
AU642711B2 (en)	1993-10-28
NZ236801A (en)	1992-11-25
AU7243891A (en)	1991-08-21
WO1991011453A2 (fr)	1991-08-08

Publication	Publication Date	Title
EP0633886B1 (fr)	2000-10-18	Amines bicycliques-heterocycliques efficaces pharmaceutiquement
US5506354A (en)	1996-04-09	Imidazolylpiperazinyl steroids
DE69111077T2 (de)	1995-11-02	Chinazolinderivate um die antitumorwirkung zu verbessern.
US5380724A (en)	1995-01-10	Piperazine and homopiperazine derivatives, pharmaceutical compositions containing them and process for preparing same
US4996318A (en)	1991-02-26	Amino-9,10-secosteroids useful for treating head injury, spinal cord trauma or stroke
EP0263213B1 (fr)	1995-09-06	Stéroides aminés en C20 à C26
WO1987001706A2 (fr)	1987-03-26	Amino-steroides c20 a c26
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Date	Code	Title	Description
1993-10-18	EEER	Examination request
1995-07-08	FZDE	Dead