CH507935A - Verfahren zur Herstellung von 2,5-Bis-(1-aziridinyl)-1,4-benzochinonderivaten - Google Patents
Verfahren zur Herstellung von 2,5-Bis-(1-aziridinyl)-1,4-benzochinonderivatenInfo
- Publication number
- CH507935A CH507935A CH130069A CH130069A CH507935A CH 507935 A CH507935 A CH 507935A CH 130069 A CH130069 A CH 130069A CH 130069 A CH130069 A CH 130069A CH 507935 A CH507935 A CH 507935A
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- benzoquinone
- radical
- group
- alkyl
- Prior art date
Links
- 229920001971 elastomer Polymers 0.000 title abstract 3
- 239000000853 adhesive Substances 0.000 title abstract 2
- 238000004026 adhesive bonding Methods 0.000 title abstract 2
- 230000001070 adhesive effect Effects 0.000 title abstract 2
- 239000004033 plastic Substances 0.000 title abstract 2
- 229920003023 plastic Polymers 0.000 title abstract 2
- -1 alkyl radical Chemical class 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 229920003986 novolac Polymers 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000008267 milk Substances 0.000 abstract 1
- 210000004080 milk Anatomy 0.000 abstract 1
- 235000013336 milk Nutrition 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920003987 resole Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000011065 in-situ storage Methods 0.000 description 8
- 208000032839 leukemia Diseases 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229940005561 1,4-benzoquinone Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- RCWJMKCTHJPXJV-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-1,4-benzoquinone Chemical class O=C1C=C(N2CC2)C(=O)C=C1N1CC1 RCWJMKCTHJPXJV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- APGBAUWQALMOFJ-UHFFFAOYSA-N 2,5-bis(2-methoxyethyl)cyclohexa-2,5-diene-1,4-dione Chemical compound COCCC=1C(C=C(C(C1)=O)CCOC)=O APGBAUWQALMOFJ-UHFFFAOYSA-N 0.000 description 2
- WIBRMGVVLZHLIF-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)-2,5-dimethoxyphenyl]ethanol Chemical compound COC1=CC(CCO)=C(OC)C=C1CCO WIBRMGVVLZHLIF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229940076286 cupric acetate Drugs 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- RCJZCRMSMQKVMA-UHFFFAOYSA-N 1-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)propan-2-yl carbamate Chemical compound CC=1C(C=C(C(C1)=O)CC(C)OC(N)=O)=O RCJZCRMSMQKVMA-UHFFFAOYSA-N 0.000 description 1
- VSWOBTLFCZYZMY-UHFFFAOYSA-N 1-[2,5-bis(aziridin-1-yl)-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]propan-2-yl carbamate Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(CC(C)OC(N)=O)=C1N1CC1 VSWOBTLFCZYZMY-UHFFFAOYSA-N 0.000 description 1
- GRLLNIGZVAQKMX-UHFFFAOYSA-N 2,5-bis(2-hydroxyethyl)cyclohexa-2,5-diene-1,4-dione Chemical compound OCCC=1C(C=C(C(C1)=O)CCO)=O GRLLNIGZVAQKMX-UHFFFAOYSA-N 0.000 description 1
- JWPJWILJETZJAQ-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-3,6-bis(2-hydroxyethyl)cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(CCO)=C(N2CC2)C(=O)C(CCO)=C1N1CC1 JWPJWILJETZJAQ-UHFFFAOYSA-N 0.000 description 1
- CHIQDKAGXLXURC-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-3,6-bis(2-methoxyethyl)cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(CCOC)=C(N2CC2)C(=O)C(CCOC)=C1N1CC1 CHIQDKAGXLXURC-UHFFFAOYSA-N 0.000 description 1
- UUOKSBAJESAYIE-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-3,6-dimethoxycyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(OC)=C(N2CC2)C(=O)C(OC)=C1N1CC1 UUOKSBAJESAYIE-UHFFFAOYSA-N 0.000 description 1
- LJIUHIQCMZRTEO-UHFFFAOYSA-N 2-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl carbamate Chemical compound CC=1C(C=C(C(C1)=O)CCOC(N)=O)=O LJIUHIQCMZRTEO-UHFFFAOYSA-N 0.000 description 1
- NNDGSCGYJFPGDK-UHFFFAOYSA-N 2-[2,5-bis(aziridin-1-yl)-3,6-dioxo-4-propylcyclohexa-1,4-dien-1-yl]ethyl carbamate Chemical compound O=C1C(CCOC(N)=O)=C(N2CC2)C(=O)C(CCC)=C1N1CC1 NNDGSCGYJFPGDK-UHFFFAOYSA-N 0.000 description 1
- XNBACIBDAYKVJC-UHFFFAOYSA-N 2-[2,5-bis(aziridin-1-yl)-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]ethyl carbamate Chemical compound O=C1C(CCOC(N)=O)=C(N2CC2)C(=O)C(C)=C1N1CC1 XNBACIBDAYKVJC-UHFFFAOYSA-N 0.000 description 1
- 125000006228 2-isobutoxyethyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FJJJAMDFWWSYCU-UHFFFAOYSA-N [2-[2,5-bis(aziridin-1-yl)-4-ethyl-3,6-dioxocyclohexa-1,4-dien-1-yl]-2-methoxyethyl] carbamate Chemical compound O=C1C(C(COC(N)=O)OC)=C(N2CC2)C(=O)C(CC)=C1N1CC1 FJJJAMDFWWSYCU-UHFFFAOYSA-N 0.000 description 1
- CLRJAKOSGSBJFY-UHFFFAOYSA-N [2-ethoxy-2-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)ethyl] carbamate Chemical compound CC=1C(C=C(C(C1)=O)C(COC(N)=O)OCC)=O CLRJAKOSGSBJFY-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP531568 | 1968-01-29 | ||
| JP4433168 | 1968-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507935A true CH507935A (de) | 1971-05-31 |
Family
ID=26339235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130069A CH507935A (de) | 1968-01-29 | 1969-01-28 | Verfahren zur Herstellung von 2,5-Bis-(1-aziridinyl)-1,4-benzochinonderivaten |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE727563A (is") |
| CH (1) | CH507935A (is") |
-
1969
- 1969-01-28 CH CH130069A patent/CH507935A/de not_active IP Right Cessation
- 1969-01-29 BE BE727563D patent/BE727563A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE727563A (is") | 1969-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |