DE2163601A1 - Arzneimittel mit einem Gehalt an (3,5,3,5-Tetraoxo)-1,2-dipiperazinoalkanverbindungen und Verfahren zur Herstellung der Verbindungen - Google Patents
Arzneimittel mit einem Gehalt an (3,5,3,5-Tetraoxo)-1,2-dipiperazinoalkanverbindungen und Verfahren zur Herstellung der VerbindungenInfo
- Publication number
- DE2163601A1 DE2163601A1 DE19712163601 DE2163601A DE2163601A1 DE 2163601 A1 DE2163601 A1 DE 2163601A1 DE 19712163601 DE19712163601 DE 19712163601 DE 2163601 A DE2163601 A DE 2163601A DE 2163601 A1 DE2163601 A1 DE 2163601A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- group
- compound
- acid
- erythro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 238000000034 method Methods 0.000 title claims description 46
- 239000003814 drug Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 8
- -1 2-hydroxyethyl-methoxymethyl Chemical group 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
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- 239000000203 mixture Substances 0.000 claims description 8
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- 239000007795 chemical reaction product Substances 0.000 claims description 6
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- 238000007363 ring formation reaction Methods 0.000 claims description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000005518 carboxamido group Chemical group 0.000 claims 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
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- 239000000243 solution Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
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- 206010028980 Neoplasm Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
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- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
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- KUDWAUANOCPTEA-UHFFFAOYSA-N 4-butylpiperazine-2,6-dione Chemical compound CCCCN1CC(=O)NC(=O)C1 KUDWAUANOCPTEA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6056470A GB1374979A (en) | 1970-12-21 | 1970-12-21 | 3,5-dioxopiperazine derivatives |
| GB710071 | 1971-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2163601A1 true DE2163601A1 (de) | 1972-06-22 |
Family
ID=26241204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163601 Pending DE2163601A1 (de) | 1970-12-21 | 1971-12-21 | Arzneimittel mit einem Gehalt an (3,5,3,5-Tetraoxo)-1,2-dipiperazinoalkanverbindungen und Verfahren zur Herstellung der Verbindungen |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU470566B2 (enrdf_load_stackoverflow) |
| BE (1) | BE776958R (enrdf_load_stackoverflow) |
| CA (1) | CA1002049A (enrdf_load_stackoverflow) |
| CH (3) | CH563997A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2163601A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2154389B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1374979A (enrdf_load_stackoverflow) |
| IL (1) | IL38342A (enrdf_load_stackoverflow) |
| SE (1) | SE400286B (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988007521A1 (en) * | 1987-03-31 | 1988-10-06 | Schering Aktiengesellschaft | Substituted complex-forming substances, complexes and complex salts, process for manufacture thereof and pharmaceutical agents which contain them |
| EP0330381A1 (en) * | 1988-02-17 | 1989-08-30 | Erbamont, Inc. | Process for preparing bis (3,5-dioxopiperazinyl) alkanes or alkenes |
| EP0409499A3 (en) * | 1989-07-13 | 1991-03-27 | National Research Development Corporation | Pharmaceutical compositions |
| US5482700A (en) * | 1987-03-31 | 1996-01-09 | Schering Aktiengesellschaft | Substituted polyamino, polycarboxy complexing agent dimers for MRI and X-ray contrast |
| US5693309A (en) * | 1987-03-31 | 1997-12-02 | Schering Aktiengesellschaft | Substituted complexing agents, complexes, and complex salts, processes for their production, and pharmaceuticals containing same |
| US6265385B1 (en) * | 1996-01-11 | 2001-07-24 | Topo Target Aps | Topoisomerase II poison and bis-dioxopiperazine derivative combination therapy |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3324235A1 (de) * | 1983-07-01 | 1985-01-10 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue komplexbildner, komplexe und komplexsalze |
| US5162372A (en) * | 1985-04-01 | 1992-11-10 | National Research Development Corporation | Pharmaceutical compositions for treating certain cancers |
| GB8508508D0 (en) * | 1985-04-01 | 1985-05-09 | Creighton A M | Pharmaceutical compositions |
| US5278187A (en) * | 1985-04-01 | 1994-01-11 | British Technology Group Ltd. | Pharmaceutical compositions |
| US5149710A (en) * | 1985-04-01 | 1992-09-22 | National Research Development Corporation | Pharmaceutical compositions for treating psoriasis |
| US5399340A (en) * | 1987-09-24 | 1995-03-21 | Schering Aktiengesellschaft | Use of amide complex compounds |
| GB2229362A (en) * | 1989-01-31 | 1990-09-26 | Kurt Hellmann | Radiosensitising compositions comprising a razoxane optical isomer |
| US5695739A (en) * | 1989-06-30 | 1997-12-09 | Schering Aktiengesellschaft | Derivatized DTPA complexes, pharmaceutical agents containing these compounds, their use, and processes for their production |
| US6039931A (en) * | 1989-06-30 | 2000-03-21 | Schering Aktiengesellschaft | Derivatized DTPA complexes, pharmaceutical agents containing these compounds, their use, and processes for their production |
| GB9115596D0 (en) * | 1991-07-12 | 1991-09-04 | Creighton Andrew M | Pharmaceutical compositions |
| GB9124483D0 (en) * | 1991-11-18 | 1992-01-08 | Windleshaw Enterprises Ltd | Bis(3,5-dioxoalkylpiperazine)derivatives for use in treating intracellular accumulation of metal ions |
| US5672335A (en) * | 1994-11-30 | 1997-09-30 | Schering Aktiengesellschaft | Use of metal complexes as liver and gallbladder X-ray diagnostic agents |
-
1970
- 1970-12-21 GB GB6056470A patent/GB1374979A/en not_active Expired
-
1971
- 1971-12-13 IL IL3834271A patent/IL38342A/xx unknown
- 1971-12-14 AU AU36837/71A patent/AU470566B2/en not_active Expired
- 1971-12-20 SE SE1635671A patent/SE400286B/xx unknown
- 1971-12-20 FR FR7145674A patent/FR2154389B2/fr not_active Expired
- 1971-12-20 CH CH246974A patent/CH563997A5/xx not_active IP Right Cessation
- 1971-12-20 CH CH1855871A patent/CH564541A5/xx not_active IP Right Cessation
- 1971-12-20 BE BE776958A patent/BE776958R/xx active
- 1971-12-20 CA CA130,520A patent/CA1002049A/en not_active Expired
- 1971-12-21 DE DE19712163601 patent/DE2163601A1/de active Pending
-
1974
- 1974-01-18 CH CH246874A patent/CH563996A5/xx not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988007521A1 (en) * | 1987-03-31 | 1988-10-06 | Schering Aktiengesellschaft | Substituted complex-forming substances, complexes and complex salts, process for manufacture thereof and pharmaceutical agents which contain them |
| US5482700A (en) * | 1987-03-31 | 1996-01-09 | Schering Aktiengesellschaft | Substituted polyamino, polycarboxy complexing agent dimers for MRI and X-ray contrast |
| US5693309A (en) * | 1987-03-31 | 1997-12-02 | Schering Aktiengesellschaft | Substituted complexing agents, complexes, and complex salts, processes for their production, and pharmaceuticals containing same |
| EP0330381A1 (en) * | 1988-02-17 | 1989-08-30 | Erbamont, Inc. | Process for preparing bis (3,5-dioxopiperazinyl) alkanes or alkenes |
| EP0409499A3 (en) * | 1989-07-13 | 1991-03-27 | National Research Development Corporation | Pharmaceutical compositions |
| US6265385B1 (en) * | 1996-01-11 | 2001-07-24 | Topo Target Aps | Topoisomerase II poison and bis-dioxopiperazine derivative combination therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2154389A2 (enrdf_load_stackoverflow) | 1973-05-11 |
| GB1374979A (en) | 1974-11-20 |
| BE776958R (fr) | 1972-06-20 |
| AU470566B2 (en) | 1976-03-18 |
| CH563997A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| FR2154389B2 (enrdf_load_stackoverflow) | 1975-11-28 |
| CA1002049A (en) | 1976-12-21 |
| CH564541A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| AU3683771A (en) | 1973-06-21 |
| CH563996A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| SE400286B (sv) | 1978-03-20 |
| IL38342A (en) | 1978-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |