SK3795A3 - Derivatives of branched aminooxyaminoalkane inhibiting the orniting decarboxylasts, pharmaceutical agent containing them and method of their production - Google Patents

Derivatives of branched aminooxyaminoalkane inhibiting the orniting decarboxylasts, pharmaceutical agent containing them and method of their production Download PDF

Info

Publication number: SK3795A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; salt; hydrogen; group
Prior art date: 1993-04-13

Application number

SK37-95A

Other languages

English (en)

Slovak (sk)

Inventor

Jorg Frei

Jaroslav Stanek

Original Assignee

Ciba Geigy Ag

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.)

1993-04-13

Filing date

1994-04-02

Publication date

1995-05-10

1994-04-02 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1995-05-10 Publication of SK3795A3 publication Critical patent/SK3795A3/sk

Links

238000000034 method Methods 0.000 title claims description 34
238000004519 manufacturing process Methods 0.000 title claims description 9
230000002401 inhibitory effect Effects 0.000 title claims description 8
239000008177 pharmaceutical agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 247
150000003839 salts Chemical class 0.000 claims abstract description 128
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
239000001257 hydrogen Substances 0.000 claims abstract description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052799 carbon Inorganic materials 0.000 claims abstract description 19
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 15
239000000203 mixture Substances 0.000 claims description 79
125000001424 substituent group Chemical group 0.000 claims description 77
125000000217 alkyl group Chemical group 0.000 claims description 62
125000006239 protecting group Chemical group 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 51
102000052812 Ornithine decarboxylases Human genes 0.000 claims description 43
108700005126 Ornithine decarboxylases Proteins 0.000 claims description 43
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
230000005764 inhibitory process Effects 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 23
238000011282 treatment Methods 0.000 claims description 21
239000008194 pharmaceutical composition Substances 0.000 claims description 16
230000008569 process Effects 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
150000001721 carbon Chemical group 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 9
125000000524 functional group Chemical group 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 5
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
230000000069 prophylactic effect Effects 0.000 claims description 4
206010037075 Protozoal infections Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
230000009471 action Effects 0.000 claims description 2
238000002405 diagnostic procedure Methods 0.000 claims description 2
DNSXKSKYVSBHSE-UHFFFAOYSA-N o-(3-amino-3-methylbutyl)hydroxylamine Chemical compound CC(C)(N)CCON DNSXKSKYVSBHSE-UHFFFAOYSA-N 0.000 claims description 2
NZRHDSUPSGWJPS-UHFFFAOYSA-N o-(3-aminobutyl)hydroxylamine Chemical compound CC(N)CCON NZRHDSUPSGWJPS-UHFFFAOYSA-N 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 2
FAUPQPXJLCGWBO-BYPYZUCNSA-N (2s)-2-amino-4-aminooxybutan-1-ol Chemical compound NOCC[C@H](N)CO FAUPQPXJLCGWBO-BYPYZUCNSA-N 0.000 claims 1
101710117642 Beta sliding clamp Proteins 0.000 claims 1
102000004031 Carboxy-Lyases Human genes 0.000 claims 1
108090000489 Carboxy-Lyases Proteins 0.000 claims 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
MXIHYLZGNQQKML-UHFFFAOYSA-N o-(3-amino-2-methylbutyl)hydroxylamine Chemical compound CC(N)C(C)CON MXIHYLZGNQQKML-UHFFFAOYSA-N 0.000 claims 1
NGPINJVGGDGVIA-UHFFFAOYSA-N o-(3-amino-2-methylpropyl)hydroxylamine Chemical compound NCC(C)CON NGPINJVGGDGVIA-UHFFFAOYSA-N 0.000 claims 1
RYMJVCWZHAIMSW-UHFFFAOYSA-N o-(3-aminopentyl)hydroxylamine Chemical compound CCC(N)CCON RYMJVCWZHAIMSW-UHFFFAOYSA-N 0.000 claims 1
NZRHDSUPSGWJPS-SCSAIBSYSA-N o-[(3r)-3-aminobutyl]hydroxylamine Chemical compound C[C@@H](N)CCON NZRHDSUPSGWJPS-SCSAIBSYSA-N 0.000 claims 1
NZRHDSUPSGWJPS-BYPYZUCNSA-N o-[(3s)-3-aminobutyl]hydroxylamine Chemical compound C[C@H](N)CCON NZRHDSUPSGWJPS-BYPYZUCNSA-N 0.000 claims 1
229960003104 ornithine Drugs 0.000 claims 1
125000006526 (C1-C2) alkyl group Chemical group 0.000 abstract 2
239000002818 ornithine decarboxylase inhibitor Substances 0.000 abstract 1
-1 40 nCi (1 Chemical compound 0.000 description 134
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
235000002639 sodium chloride Nutrition 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
125000002887 hydroxy group Chemical group [H]O* 0.000 description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
239000002253 acid Substances 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 41
239000002904 solvent Substances 0.000 description 40
238000010992 reflux Methods 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
239000007858 starting material Substances 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
239000000741 silica gel Substances 0.000 description 28
229910002027 silica gel Inorganic materials 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
239000002585 base Substances 0.000 description 25
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 24
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 description 22
229910052757 nitrogen Inorganic materials 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
102000016893 Amine Oxidase (Copper-Containing) Human genes 0.000 description 19
108010028700 Amine Oxidase (Copper-Containing) Proteins 0.000 description 19
125000002252 acyl group Chemical group 0.000 description 18
238000001704 evaporation Methods 0.000 description 17
230000008020 evaporation Effects 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
239000004480 active ingredient Substances 0.000 description 16
239000003112 inhibitor Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
125000005843 halogen group Chemical group 0.000 description 13
239000003921 oil Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 12
125000003277 amino group Chemical group 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
229920000768 polyamine Polymers 0.000 description 12
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
229910052783 alkali metal Inorganic materials 0.000 description 10
125000001118 alkylidene group Chemical group 0.000 description 10
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
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 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 9
108090000790 Enzymes Proteins 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
150000008044 alkali metal hydroxides Chemical class 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
150000004292 cyclic ethers Chemical class 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
230000008030 elimination Effects 0.000 description 7
238000003379 elimination reaction Methods 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
239000012071 phase Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
230000009467 reduction Effects 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
239000003826 tablet Substances 0.000 description 7
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
239000005700 Putrescine Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000003125 aqueous solvent Substances 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
238000009835 boiling Methods 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
238000011065 in-situ storage Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000003797 solvolysis reaction Methods 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
150000001450 anions Chemical class 0.000 description 5
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
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238000004587 chromatography analysis Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000008096 xylene Substances 0.000 description 5
CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
125000005103 alkyl silyl group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
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QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
150000002545 isoxazoles Chemical class 0.000 description 1
238000002386 leaching Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910001512 metal fluoride Inorganic materials 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910001511 metal iodide Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
PHNRCFCIKPZSFS-UHFFFAOYSA-N n'-tert-butyl-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC(C)(C)C PHNRCFCIKPZSFS-UHFFFAOYSA-N 0.000 description 1
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000017095 negative regulation of cell growth Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
108020004707 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
UYHRYYSZTRWFKE-UHFFFAOYSA-N o-(3-aminopentyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CCC(N)CCON UYHRYYSZTRWFKE-UHFFFAOYSA-N 0.000 description 1
VSZFWDPIWSPZON-UHFFFAOYSA-N o-(3-aminopropyl)hydroxylamine Chemical compound NCCCON VSZFWDPIWSPZON-UHFFFAOYSA-N 0.000 description 1
MNKPVSOWLRMBKE-UHFFFAOYSA-N o-(4-aminobutan-2-yl)hydroxylamine Chemical compound NOC(C)CCN MNKPVSOWLRMBKE-UHFFFAOYSA-N 0.000 description 1
NCBWTMFLUNRAOL-RZFWHQLPSA-N o-[(3r)-3-aminobutyl]hydroxylamine;dihydrochloride Chemical compound Cl.Cl.C[C@@H](N)CCON NCBWTMFLUNRAOL-RZFWHQLPSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
210000001236 prokaryotic cell Anatomy 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
239000003881 protein kinase C inhibitor Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
231100000161 signs of toxicity Toxicity 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
238000009492 tablet coating Methods 0.000 description 1
IDXKPWMYURAXTA-UHFFFAOYSA-N tert-butyl n-(3-hydroxybutyl)carbamate Chemical compound CC(O)CCNC(=O)OC(C)(C)C IDXKPWMYURAXTA-UHFFFAOYSA-N 0.000 description 1
QHSUFODBDZQCHO-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2-methylbutan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCO QHSUFODBDZQCHO-UHFFFAOYSA-N 0.000 description 1
JSZOAOLSEKSNTD-UHFFFAOYSA-N tert-butyl n-(4-hydroxybutan-2-yl)carbamate Chemical compound OCCC(C)NC(=O)OC(C)(C)C JSZOAOLSEKSNTD-UHFFFAOYSA-N 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005891 transamination reaction Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005039 triarylmethyl group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
201000002311 trypanosomiasis Diseases 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
238000005353 urine analysis Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK37-95A 1993-04-13 1994-04-02 Derivatives of branched aminooxyaminoalkane inhibiting the orniting decarboxylasts, pharmaceutical agent containing them and method of their production SK3795A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH112993		1993-04-13
PCT/EP1994/001036 WO1994024094A1 (fr)	1993-04-13	1994-04-02	Derives d'alcane amino aminooxy a chaine ramifiee inhibiteurs de la decarboxylase d'ornithine

Publications (1)

Publication Number	Publication Date
SK3795A3 true SK3795A3 (en)	1995-05-10

Family

ID=4203174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK37-95A SK3795A3 (en)	1993-04-13	1994-04-02	Derivatives of branched aminooxyaminoalkane inhibiting the orniting decarboxylasts, pharmaceutical agent containing them and method of their production

Country Status (18)

Country	Link
US (1)	US5610195A (fr)
EP (1)	EP0644873B1 (fr)
JP (1)	JPH07508046A (fr)
CN (1)	CN1034930C (fr)
AT (1)	ATE150009T1 (fr)
AU (1)	AU673073B2 (fr)
CA (1)	CA2135781A1 (fr)
CZ (1)	CZ7995A3 (fr)
DE (1)	DE69402021T2 (fr)
DK (1)	DK0644873T3 (fr)
ES (1)	ES2102221T3 (fr)
GR (1)	GR3023429T3 (fr)
HU (1)	HUT72751A (fr)
NZ (1)	NZ265253A (fr)
PL (1)	PL306765A1 (fr)
RU (1)	RU95110939A (fr)
SK (1)	SK3795A3 (fr)
WO (1)	WO1994024094A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU95110887A (ru) *	1993-04-13	1996-10-27	Циба-Гейги АГ (CH)	Ингибирующие орнитин-декарбоксилазу циклические аминоокисления
US20030166554A1 (en) *	2001-01-16	2003-09-04	Genset, S.A.	Treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase antagonists
US20030185754A1 (en) *	2001-01-16	2003-10-02	Genset, S.A.	Treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase antagonists

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB974163A (en) *	1960-04-08	1964-11-04	Ciba Ltd	Manufacture of 1-amino-ªÏ-hydroxylamino-alkanes
US3137705A (en) *	1960-04-08	1964-06-16	Ciba Geigy Corp	Hydroxylamino compounds
US3869278A (en) *	1972-07-27	1975-03-04	Merrill Wilcox	Hydroxylamines and derivatives thereof as abscission agents
US4390534A (en) *	1978-12-29	1983-06-28	Fujisawa Pharmaceutical Co., Ltd.	Cephem and cepham compounds
DE3501616A1 (de) *	1985-01-17	1986-07-17	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von hydroxylamin-derivaten
US4853467A (en) *	1987-05-19	1989-08-01	Bristol-Myers Company	Nitrogen containing derivatives of epipodophyllotoxin glucosides
GB8729521D0 (en) *	1987-12-18	1988-02-03	May & Baker Ltd	New compositions of matter
EP0369944A1 (fr) *	1988-11-18	1990-05-23	Ciba-Geigy Ag	Oxadiaminobutanes substitués
CA2014880A1 (fr) *	1989-04-27	1990-10-27	Indu Sawhney	Derives du thiazole
NO903360L (no) *	1989-08-11	1991-02-12	Ici Pharma	Antibiotiske forbindelser.
EP0483427A1 (fr) *	1990-11-01	1992-05-06	The Procter & Gamble Company	Composition déodorante et méthode de déodorisation à l'aide d'amine
RU95110887A (ru) *	1993-04-13	1996-10-27	Циба-Гейги АГ (CH)	Ингибирующие орнитин-декарбоксилазу циклические аминоокисления

1994
- 1994-04-02 DK DK94913517.2T patent/DK0644873T3/da not_active Application Discontinuation
- 1994-04-02 ES ES94913517T patent/ES2102221T3/es not_active Expired - Lifetime
- 1994-04-02 US US08/351,336 patent/US5610195A/en not_active Expired - Fee Related
- 1994-04-02 CZ CZ9579A patent/CZ7995A3/cs unknown
- 1994-04-02 SK SK37-95A patent/SK3795A3/sk unknown
- 1994-04-02 RU RU95110939/04A patent/RU95110939A/ru unknown
- 1994-04-02 DE DE69402021T patent/DE69402021T2/de not_active Expired - Fee Related
- 1994-04-02 HU HU9500095A patent/HUT72751A/hu unknown
- 1994-04-02 PL PL94306765A patent/PL306765A1/xx unknown
- 1994-04-02 WO PCT/EP1994/001036 patent/WO1994024094A1/fr not_active Ceased
- 1994-04-02 AU AU65646/94A patent/AU673073B2/en not_active Ceased
- 1994-04-02 CA CA002135781A patent/CA2135781A1/fr not_active Abandoned
- 1994-04-02 AT AT94913517T patent/ATE150009T1/de not_active IP Right Cessation
- 1994-04-02 JP JP6522690A patent/JPH07508046A/ja active Pending
- 1994-04-02 EP EP94913517A patent/EP0644873B1/fr not_active Expired - Lifetime
- 1994-04-02 NZ NZ265253A patent/NZ265253A/en unknown
- 1994-04-02 CN CN94190189A patent/CN1034930C/zh not_active Expired - Fee Related
1997
- 1997-05-15 GR GR970401078T patent/GR3023429T3/el unknown

Also Published As

Publication number	Publication date
GR3023429T3 (en)	1997-08-29
ES2102221T3 (es)	1997-07-16
HUT72751A (en)	1996-05-28
RU95110939A (ru)	1996-10-27
WO1994024094A1 (fr)	1994-10-27
CN1104831A (zh)	1995-07-05
CZ7995A3 (en)	1995-10-18
CA2135781A1 (fr)	1994-10-27
PL306765A1 (en)	1995-04-18
NZ265253A (en)	1996-10-28
US5610195A (en)	1997-03-11
DE69402021D1 (en)	1997-04-17
DK0644873T3 (da)	1997-04-07
EP0644873B1 (fr)	1997-03-12
JPH07508046A (ja)	1995-09-07
AU6564694A (en)	1994-11-08
ATE150009T1 (de)	1997-03-15
HU9500095D0 (en)	1995-03-28
EP0644873A1 (fr)	1995-03-29
DE69402021T2 (de)	1997-10-30
AU673073B2 (en)	1996-10-24
CN1034930C (zh)	1997-05-21

Publication	Publication Date	Title
FI112472B (fi)	2003-12-15	Menetelmä terapeuttisesti aktiivisten substituoitujen atsaheterosyklikarboksyylihappojen valmistamiseksi
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