DD234017A5 - Verfahre zur herstellung von oxazaphosphorin-derivaten - Google Patents

Verfahre zur herstellung von oxazaphosphorin-derivaten Download PDF

Info

Publication number: DD234017A5
Authority: DD; German Democratic Republic
Prior art keywords: group; compound; salt; amino; formula
Prior art date: 1984-03-01

Application number

DD85273643A

Other languages

German (de)

English (en)

Inventor

Juergen Engel

Axel Kleemann

Ulf Niemeyer

Peter Hilgard

Joerg Pohl

Original Assignee

��`��@��k��@��k��

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.)

1984-03-01

Filing date

1985-02-28

Publication date

1986-03-19

1985-02-28 Application filed by ��`��@��k��@��k�� filed Critical ��`��@��k��@��k��

1986-03-19 Publication of DD234017A5 publication Critical patent/DD234017A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 18
ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical class N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 title claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 80
150000001875 compounds Chemical class 0.000 claims abstract description 68
-1 2-methanesulfonoyloxyethyl Chemical group 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 31
KIWQWJKWBHZMDT-UHFFFAOYSA-N homocysteine thiolactone Chemical compound NC1CCSC1=O KIWQWJKWBHZMDT-UHFFFAOYSA-N 0.000 claims abstract description 19
150000007514 bases Chemical class 0.000 claims abstract description 18
150000002431 hydrogen Chemical class 0.000 claims abstract description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
125000003277 amino group Chemical group 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
239000000872 buffer Substances 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 16
150000001447 alkali salts Chemical class 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
229940126062 Compound A Drugs 0.000 claims description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
KATOCNXVWLJLIU-UHFFFAOYSA-N 3-amino-3-(difluoromethyl)piperidin-2-one Chemical compound FC(F)C1(N)CCCNC1=O KATOCNXVWLJLIU-UHFFFAOYSA-N 0.000 claims description 2
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical group O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 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
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
229940124531 pharmaceutical excipient Drugs 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 5
125000001041 indolyl group Chemical group 0.000 abstract description 4
229910006069 SO3H Inorganic materials 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
231100000053 low toxicity Toxicity 0.000 abstract 1
230000009897 systematic effect Effects 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 34
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150000002500 ions Chemical class 0.000 description 23
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238000006243 chemical reaction Methods 0.000 description 16
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
150000001768 cations Chemical class 0.000 description 12
229960004397 cyclophosphamide Drugs 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
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150000003254 radicals Chemical class 0.000 description 11
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230000002378 acidificating effect Effects 0.000 description 10
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239000001509 sodium citrate Substances 0.000 description 9
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 9
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235000019766 L-Lysine Nutrition 0.000 description 7
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 description 5
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239000004480 active ingredient Substances 0.000 description 5
239000007979 citrate buffer Substances 0.000 description 5
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
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 description 4
101000623895 Bos taurus Mucin-15 Proteins 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000003862 amino acid derivatives Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229960004635 mesna Drugs 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 4
125000000542 sulfonic acid group Chemical group 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
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239000007795 chemical reaction product Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
229940102223 injectable solution Drugs 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000008174 sterile solution Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
AOVSQSOPHMZKBH-JEDNCBNOSA-N (2S)-2,6-diaminohexanoic acid 2-sulfanylethanesulfonic acid Chemical compound OS(=O)(=O)CCS.NCCCC[C@H](N)C(O)=O AOVSQSOPHMZKBH-JEDNCBNOSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
235000009697 arginine Nutrition 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
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ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000003946 cyclohexylamines Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
150000002019 disulfides Chemical class 0.000 description 2
238000010828 elution Methods 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000001506 immunosuppresive effect Effects 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
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LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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150000003573 thiols Chemical class 0.000 description 2
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230000001988 toxicity Effects 0.000 description 2
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MPOCIPREOMFUSB-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound NCCCC[C@H](N)C(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O MPOCIPREOMFUSB-JEDNCBNOSA-N 0.000 description 1
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BXRMEWOQUXOLDH-LURJTMIESA-N L-Histidine methyl ester Chemical compound COC(=O)[C@@H](N)CC1=CN=CN1 BXRMEWOQUXOLDH-LURJTMIESA-N 0.000 description 1
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ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical compound NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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239000012928 buffer substance Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
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LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002949 hemolytic effect Effects 0.000 description 1
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230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
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125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000002624 leukotoxic effect Effects 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000011068 loading method Methods 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
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239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
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239000005011 phenolic resin Substances 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
239000004324 sodium propionate Substances 0.000 description 1
235000010334 sodium propionate Nutrition 0.000 description 1
229960003212 sodium propionate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
NSFFHOGKXHRQEW-AIHSUZKVSA-N thiostrepton Chemical compound C([C@]12C=3SC=C(N=3)C(=O)N[C@H](C(=O)NC(/C=3SC[C@@H](N=3)C(=O)N[C@H](C=3SC=C(N=3)C(=O)N[C@H](C=3SC=C(N=3)[C@H]1N=1)[C@@H](C)OC(=O)C3=CC(=C4C=C[C@H]([C@@H](C4=N3)O)N[C@H](C(N[C@@H](C)C(=O)NC(=C)C(=O)N[C@@H](C)C(=O)N2)=O)[C@@H](C)CC)[C@H](C)O)[C@](C)(O)[C@@H](C)O)=C\C)[C@@H](C)O)CC=1C1=NC(C(=O)NC(=C)C(=O)NC(=C)C(N)=O)=CS1 NSFFHOGKXHRQEW-AIHSUZKVSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 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
230000017105 transposition Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
FONYLINGKWPNNY-UHFFFAOYSA-K trisodium prop-1-ene-1,2,3-tricarboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(=CC([O-])=O)C([O-])=O FONYLINGKWPNNY-UHFFFAOYSA-K 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD85273643A 1984-03-01 1985-02-28 Verfahre zur herstellung von oxazaphosphorin-derivaten DD234017A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3407585		1984-03-01

Publications (1)

Publication Number	Publication Date
DD234017A5 true DD234017A5 (de)	1986-03-19

Family

ID=6229317

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85273643A DD234017A5 (de)	1984-03-01	1985-02-28	Verfahre zur herstellung von oxazaphosphorin-derivaten

Country Status (9)

Country	Link
US (1)	US4716242A (da)
JP (1)	JPH072757B2 (da)
DD (1)	DD234017A5 (da)
DK (1)	DK93985A (da)
ES (1)	ES540778A0 (da)
PL (2)	PL146149B1 (da)
PT (1)	PT80024B (da)
YU (2)	YU31285A (da)
ZA (1)	ZA851062B (da)

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DE58900183D1 (de) *	1988-03-19	1991-08-29	Asta Pharma Ag	Ifosfamid-mesna-lyophilisat und verfahren zu dessen herstellung.
DE3835772A1 (de) *	1988-10-20	1990-04-26	Deutsches Krebsforsch	Tumorhemmende saccharid-konjugate
US5227373A (en) *	1991-10-23	1993-07-13	Bristol-Myers Squibb Co.	Lyophilized ifosfamide compositions
US6828415B2 (en)	1993-02-19	2004-12-07	Zentaris Gmbh	Oligopeptide lyophilisate, their preparation and use
US5873584A (en) *	1995-01-17	1999-02-23	Rike Inline, Inc.	In-line roller skate frame
DE102004031569A1 (de) *	2004-06-29	2006-02-02	Baxter International Inc., Deerfield	Verfahren zur Herstellung von lagerstabiler Mafosfamid-Lysin-Salz Lyophilisat Bulkware und zu dessen Weiterverarbeitung zu Mafosfamid-Lysin-Salz Lyophilisat in dosierter Form
EP2336140B1 (en) *	2004-10-25	2016-01-27	Dekk-Tec, Inc.	Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents
AU2010218109B2 (en) *	2009-02-24	2015-04-09	Dekk-Tec, Inc.	Complexes of 4-hydroperoxy ifosfamide as anti-tumor agents

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5159886A (da) *	1974-11-20	1976-05-25	Shionogi Seiyaku Kk
US4220660A (en) *	1977-12-14	1980-09-02	Asta-werke Aktiengesellschaft, Chemische Farik	Process for the treatment of humans suffering from undesired urotoxic side effects caused by cytostatically active alkylating agents
JPS54157580A (en) *	1978-05-29	1979-12-12	Otsuka Pharmaceut Co Ltd	Optically active oxazaphosphorine derivative
JPS5651184A (en) *	1979-10-03	1981-05-08	Hitachi Ltd	Color solid image pickup device
DE3133309A1 (de) *	1980-09-10	1982-04-15	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	4-carbamoyloxy-oxazaphosphorine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
DE3220432A1 (de) *	1981-03-24	1983-12-01	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	Oxazaphosphorin-4-thio-alkansulfonsaeure, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate
DE3220672A1 (de) *	1981-03-24	1983-12-08	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	Cis-oxazaphosphorin-4-thio-alkansulfonsaeuren, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate
DE3111428A1 (de) *	1981-03-24	1982-10-07	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
DE3132221A1 (de) *	1981-08-14	1983-05-19	Behringwerke Ag, 3550 Marburg	Neue cyclophosphamid-derivate, verfahren zu ihrer herstellung und ihre verwendung
DE3133077A1 (de) *	1981-08-21	1983-03-10	Henkel KGaA, 4000 Düsseldorf	Neue cytostatisch wirksame epoxidgruppen tragende 1,3,2-oxazaphosphorin-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung in pharmazeutischen zubereitungen
US4618692A (en) *	1981-09-03	1986-10-21	Asta-Werke Aktiengesellschaft	4-carbamoyloxy-oxazaphosphorins
DE3247436A1 (de) *	1981-12-31	1983-07-14	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	4-sulfido-oxazaphosphorine und deren verwendung bei der krebsbekaempfung und zur immunsuppression
EP0083439B1 (de) *	1981-12-31	1989-07-26	ASTA Pharma AG	4-Sulfido-oxazaphosphorine und deren Verwendung bei der Krebsbekämpfung und zur Immunsuppression
DE3505482A1 (de) *	1984-03-01	1985-09-05	Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld	Neue salze von oxazaphosphorin-derivaten

1985
- 1985-02-12 ZA ZA851062A patent/ZA851062B/xx unknown
- 1985-02-22 US US06/704,465 patent/US4716242A/en not_active Expired - Lifetime
- 1985-02-28 ES ES540778A patent/ES540778A0/es active Granted
- 1985-02-28 PL PL1985266394A patent/PL146149B1/pl unknown
- 1985-02-28 DK DK93985A patent/DK93985A/da not_active Application Discontinuation
- 1985-02-28 DD DD85273643A patent/DD234017A5/de unknown
- 1985-02-28 YU YU00312/85A patent/YU31285A/xx unknown
- 1985-02-28 PL PL1985252161A patent/PL143712B1/pl unknown
- 1985-02-28 PT PT80024A patent/PT80024B/pt unknown
- 1985-03-01 JP JP60038978A patent/JPH072757B2/ja not_active Expired - Fee Related
1987
- 1987-06-26 YU YU01202/87A patent/YU120287A/xx unknown

Also Published As

Publication number	Publication date
ES8602831A1 (es)	1985-12-01
US4716242A (en)	1987-12-29
YU31285A (en)	1988-02-29
PT80024A (de)	1985-03-01
DK93985D0 (da)	1985-02-28
PL252161A1 (en)	1986-08-26
JPH072757B2 (ja)	1995-01-18
DK93985A (da)	1985-09-02
YU120287A (en)	1988-04-30
ZA851062B (en)	1985-11-27
PT80024B (pt)	1987-09-18
JPS60222494A (ja)	1985-11-07
PL146149B1 (en)	1988-12-31
ES540778A0 (es)	1985-12-01
PL143712B1 (en)	1988-03-31

Publication	Publication Date	Title
DE2332878C2 (de)	1983-07-28	Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen
DE69414720T2 (de)	1999-04-08	Kristallines, wasserfreies mofetilmycophenolat und zubereitungen zu deren intravenösen anwendung
DD141520A5 (de)	1980-05-07	Verfahren zur herstellung neuer derivate von 4-amino-5-alkylsulfonyl-ortho-anisamiden
DE69433793T2 (de)	2005-05-04	Phosphorderivate zur behandlung von aids
DE69725696T2 (de)	2004-07-29	Carbapenem-antibiotikum, zusammensetzung und ihre herstellung
WO1997032865A1 (de)	1997-09-12	Neue arylglycinamidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen
DE2527914A1 (de)	1976-01-02	Vincaminverbindungen, verfahren zu deren herstellung sowie diese enthaltende pharmazeutische mittel
EP0498380A1 (de)	1992-08-12	Komplexbildner
DE1670935B2 (de)	1975-04-24	2-Methyl-3-carbonsäureamidochinoxalin-1,4-di-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
DE3885031T2 (de)	1994-02-17	Wasserlösliches antibiotisches Präparat und wasserlösliche Salze von Cephem-Verbindungen.
EP0158057B1 (de)	1989-04-26	Neue Salze von Oxazaphosphorin-Derivaten
DD235637A5 (de)	1986-05-14	Verfahren zur herstellung von amidinverbindungen
DE2119964B2 (de)	1973-05-10	Methyl-n-(n'-methyl-n'-nitrosocarbamoyl)-d-glycosaminid und verfahren zu dessen herstellung
DE1807165A1 (de)	1969-06-12	Neue 4H-1,3-Benzothiazin-4-one
US4716242A (en)	1987-12-29	Salts of oxazaphosphorine derivatives
DE3505482A1 (de)	1985-09-05	Neue salze von oxazaphosphorin-derivaten
DE2711149C3 (de)	1980-12-11	N-Substituierte[4-Chlor-6-(23-xylidino)-2· pyrimidinyl- thio] essigsäureamide sowie Verfahren zu deren Herstellung
DD248592A5 (de)	1987-08-12	Verfahren zur herstellung der [3s(z)]-2-[1-(2-amino-4-thiazolyl)-2-[[2,2-dimethyl-4-oxo-1-(sulfoxy)-3-azetidinyl]-amino]-2-oxoaethyliden]-aminooxyessigsaeure und ihrer salze
CH649998A5 (de)	1985-06-28	Ergolinderivate, ein verfahren zu ihrer herstellung und heilmittel, enthaltend diese ergolinderivate als wirkstoff.
DE69322081T2 (de)	1999-07-08	Salze von chinolon carbonsäuren
DE2927452A1 (de)	1980-01-17	Neue derivate des daunorubicins, ihre herstellung und die sie enthaltenden pharmazeutischen zusammensetzungen
DE3220672A1 (de)	1983-12-08	Cis-oxazaphosphorin-4-thio-alkansulfonsaeuren, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate
DE3782229T2 (de)	1993-03-04	Verwendung von 2-oxo-imidazolidin-derivaten zur behandlung von nierenkrankheiten.
DE3102026C2 (da)	1990-05-31
DE1545838C3 (de)	1975-12-11	7-(2-Azidooctanamido)-cephalosporansäure, deren Salze und Verfahren zur Herstellung dieser Verbindungen