CH520694A - Verfahren zur Herstellung von Phenazin-Derivaten - Google Patents
Verfahren zur Herstellung von Phenazin-DerivatenInfo
- Publication number
- CH520694A CH520694A CH1048171A CH1048171A CH520694A CH 520694 A CH520694 A CH 520694A CH 1048171 A CH1048171 A CH 1048171A CH 1048171 A CH1048171 A CH 1048171A CH 520694 A CH520694 A CH 520694A
- Authority
- CH
- Switzerland
- Prior art keywords
- dioxide
- chloroform
- phenazine
- formula
- reaction
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 title 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 4
- ZMFJCQAPRNRDSK-UHFFFAOYSA-N 10-oxidophenazin-5-ium 5-oxide Chemical compound C1=CC=C2N([O-])C3=CC=CC=C3[N+](=O)C2=C1 ZMFJCQAPRNRDSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SFNYAHCOEPIPGO-UHFFFAOYSA-N 1,6-dimethoxyphenazine Chemical compound C1=CC=C2N=C3C(OC)=CC=CC3=NC2=C1OC SFNYAHCOEPIPGO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- -1 1,6-disubstituted phenazine Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OGNXLFBCXQYFDB-UHFFFAOYSA-N 1,6-dimethoxyphenazine N(5),N(10)-dioxide Chemical compound [O-]N1C2=CC=CC(OC)=C2[N+](=O)C2=C1C(OC)=CC=C2 OGNXLFBCXQYFDB-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- NBMOVCYIGUDQJE-UHFFFAOYSA-N iodinin Chemical compound C1=CC=C2[N+]([O-])=C3C(O)=CC=CC3=[N+]([O-])C2=C1O NBMOVCYIGUDQJE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JIDVGUQUQSOHOL-UHFFFAOYSA-N myxin Chemical compound C1=CC=C2[N+]([O-])=C3C(OC)=CC=CC3=[N+]([O-])C2=C1O JIDVGUQUQSOHOL-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 150000002988 phenazines Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- GWAAUIUHEAGBBM-UHFFFAOYSA-N 1,6-bis(phenylmethoxy)phenazine Chemical compound C(C1=CC=CC=C1)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC1=CC=CC=C1 GWAAUIUHEAGBBM-UHFFFAOYSA-N 0.000 description 2
- JOXNFMAXWAPITK-UHFFFAOYSA-N 1,6-dihydroxyphenazine Chemical compound C1=CC=C2N=C3C(O)=CC=CC3=NC2=C1O JOXNFMAXWAPITK-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- BMINBRPDZDJGSU-UHFFFAOYSA-N C(C)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC Chemical compound C(C)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC BMINBRPDZDJGSU-UHFFFAOYSA-N 0.000 description 2
- GPXMBAKKHRSRHU-UHFFFAOYSA-N COC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC Chemical compound COC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC GPXMBAKKHRSRHU-UHFFFAOYSA-N 0.000 description 2
- PZJDTLYEGJQMPR-UHFFFAOYSA-N COC1=CC=CC2=[N+](C3=C(C=CC=C3[N+](=C12)[O-])OCC)[O-] Chemical compound COC1=CC=CC2=[N+](C3=C(C=CC=C3[N+](=C12)[O-])OCC)[O-] PZJDTLYEGJQMPR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007361 Wohl-Aue reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005661 deetherification reaction Methods 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YJPUKVVGBLRGID-UHFFFAOYSA-N 1,6-dimethoxyphenazine N(5)-oxide Chemical compound C1=CC=C2N=C3C(OC)=CC=CC3=[N+]([O-])C2=C1OC YJPUKVVGBLRGID-UHFFFAOYSA-N 0.000 description 1
- VBYCMICBXHTQHS-UHFFFAOYSA-N 1,6-dipropoxyphenazine Chemical compound C(CC)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCCC VBYCMICBXHTQHS-UHFFFAOYSA-N 0.000 description 1
- CYNFKYWHXHKBEN-UHFFFAOYSA-N 1-ethoxy-6-propoxyphenazine Chemical compound C(C)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCCC CYNFKYWHXHKBEN-UHFFFAOYSA-N 0.000 description 1
- FHYXQMGMICVTGE-UHFFFAOYSA-N 1-methoxy-6-phenylmethoxyphenazine Chemical compound C(C1=CC=CC=C1)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OC FHYXQMGMICVTGE-UHFFFAOYSA-N 0.000 description 1
- FJUMKIYHOCPWEZ-UHFFFAOYSA-N 1-methoxy-6-propoxyphenazine Chemical compound COC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCCC FJUMKIYHOCPWEZ-UHFFFAOYSA-N 0.000 description 1
- UVACTLPZMXQYAK-UHFFFAOYSA-N 1-phenylmethoxy-6-propoxyphenazine Chemical compound C(C1=CC=CC=C1)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCCC UVACTLPZMXQYAK-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- LBBOLLVFOUUAOU-UHFFFAOYSA-N 6-ethoxy-1-methoxy-5-oxidophenazin-5-ium Chemical compound COC1=CC=CC2=[N+](C3=C(C=CC=C3N=C12)OCC)[O-] LBBOLLVFOUUAOU-UHFFFAOYSA-N 0.000 description 1
- JBLMDWVOUDUDBG-UHFFFAOYSA-N 6-ethoxy-5,10-dioxidophenazine-5,10-diium-1-ol Chemical compound C(C)OC1=C2[N+](=C3C=CC=C(C3=[N+](C2=CC=C1)[O-])O)[O-] JBLMDWVOUDUDBG-UHFFFAOYSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001430355 Brevibacterium iodinum Species 0.000 description 1
- ROOKNWGFGPIAOV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC Chemical compound C(C1=CC=CC=C1)OC1=CC=CC2=NC3=C(C=CC=C3N=C12)OCC ROOKNWGFGPIAOV-UHFFFAOYSA-N 0.000 description 1
- XSVZDOAQWCVXTR-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=CC=CC2=[N+](C3=C(C=CC=C3N=C12)OCC1=CC=CC=C1)[O-] Chemical compound C(C1=CC=CC=C1)OC1=CC=CC2=[N+](C3=C(C=CC=C3N=C12)OCC1=CC=CC=C1)[O-] XSVZDOAQWCVXTR-UHFFFAOYSA-N 0.000 description 1
- JUDKQQVKCWVNQZ-UHFFFAOYSA-N COC1=CC=CC2=NC3=C(C=CC=C3[N+](=C12)[O-])OCC Chemical compound COC1=CC=CC2=NC3=C(C=CC=C3[N+](=C12)[O-])OCC JUDKQQVKCWVNQZ-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- RGZOLFGLBMQRDV-UHFFFAOYSA-N [IH]1CC=CC=C1.C1(=CC=CC2=[N+](C=3C(=CC=CC3[N+](=C12)[O-])O)[O-])O Chemical compound [IH]1CC=CC=C1.C1(=CC=CC2=[N+](C=3C(=CC=CC3[N+](=C12)[O-])O)[O-])O RGZOLFGLBMQRDV-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vehicle Body Suspensions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59679466A | 1966-11-25 | 1966-11-25 | |
| CH1560067A CH512500A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazin-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH520694A true CH520694A (de) | 1972-03-31 |
Family
ID=24388733
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1048171A CH520694A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazin-Derivaten |
| CH503670A CH521358A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazinderivaten |
| CH1560067A CH512500A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazin-Derivaten |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH503670A CH521358A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazinderivaten |
| CH1560067A CH512500A (de) | 1966-11-25 | 1967-11-08 | Verfahren zur Herstellung von Phenazin-Derivaten |
Country Status (14)
| Country | Link |
|---|---|
| AT (2) | AT281852B (enEXAMPLES) |
| BE (1) | BE706861A (enEXAMPLES) |
| CA (1) | CA946397A (enEXAMPLES) |
| CH (3) | CH520694A (enEXAMPLES) |
| DE (2) | DE1795724C3 (enEXAMPLES) |
| ES (1) | ES347576A1 (enEXAMPLES) |
| FR (1) | FR1545331A (enEXAMPLES) |
| GB (1) | GB1142448A (enEXAMPLES) |
| GR (1) | GR38359B (enEXAMPLES) |
| IL (1) | IL28972A (enEXAMPLES) |
| NL (2) | NL6715787A (enEXAMPLES) |
| NO (1) | NO123528B (enEXAMPLES) |
| PH (2) | PH11778A (enEXAMPLES) |
| SE (3) | SE366985B (enEXAMPLES) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH532589A (de) * | 1969-05-14 | 1973-01-15 | Hoffmann La Roche | Verfahren zur Herstellung von Phenazin-Derivaten |
| US3681331A (en) * | 1970-04-02 | 1972-08-01 | Hoffmann La Roche | 1-hydroxy-6-amino alkoxy-phenazine 5,10-dioxides |
| CH575213A5 (enEXAMPLES) * | 1972-09-05 | 1976-05-14 | Ciba Geigy Ag | |
| CN104974100A (zh) * | 2015-07-07 | 2015-10-14 | 江苏省农业科学院 | 来源于抗生素溶杆菌oh13的吩嗪类化合物及其制备方法与应用 |
-
1967
- 1967-11-08 CH CH1048171A patent/CH520694A/de not_active IP Right Cessation
- 1967-11-08 CH CH503670A patent/CH521358A/de not_active IP Right Cessation
- 1967-11-08 CH CH1560067A patent/CH512500A/de not_active IP Right Cessation
- 1967-11-10 DE DE19671795724 patent/DE1795724C3/de not_active Expired
- 1967-11-10 DE DE19671695212 patent/DE1695212B2/de active Granted
- 1967-11-20 GR GR670138359A patent/GR38359B/el unknown
- 1967-11-20 IL IL2897267A patent/IL28972A/xx unknown
- 1967-11-20 CA CA005,531A patent/CA946397A/en not_active Expired
- 1967-11-21 NL NL6715787A patent/NL6715787A/xx unknown
- 1967-11-22 AT AT01136/69A patent/AT281852B/de not_active IP Right Cessation
- 1967-11-22 BE BE706861A patent/BE706861A/fr unknown
- 1967-11-22 GB GB5320167A patent/GB1142448A/en not_active Expired
- 1967-11-22 SE SE1781070A patent/SE366985B/xx unknown
- 1967-11-22 SE SE43872A patent/SE366988B/xx unknown
- 1967-11-22 SE SE1607067A patent/SE349036B/xx unknown
- 1967-11-22 AT AT1053467A patent/AT281851B/de not_active IP Right Cessation
- 1967-11-24 NO NO17069767A patent/NO123528B/no unknown
- 1967-11-24 ES ES347576A patent/ES347576A1/es not_active Expired
- 1967-11-24 FR FR129677A patent/FR1545331A/fr not_active Expired
-
1972
- 1972-01-03 PH PH13146A patent/PH11778A/en unknown
-
1974
- 1974-07-15 NL NL7409550A patent/NL7409550A/xx unknown
-
1976
- 1976-01-19 PH PH17992A patent/PH12441A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695212C3 (enEXAMPLES) | 1974-09-19 |
| CH521358A (de) | 1972-04-15 |
| SE366988B (enEXAMPLES) | 1974-05-13 |
| SE349036B (enEXAMPLES) | 1972-09-18 |
| DE1695212A1 (de) | 1971-03-18 |
| PH12441A (en) | 1979-03-01 |
| NL6715787A (enEXAMPLES) | 1968-05-27 |
| NO123528B (enEXAMPLES) | 1971-12-06 |
| IL28972A (en) | 1973-03-30 |
| DE1795724B2 (de) | 1978-09-28 |
| GR38359B (el) | 1969-10-30 |
| PH11778A (en) | 1978-07-05 |
| AT281852B (enEXAMPLES) | 1970-06-10 |
| GB1142448A (en) | 1969-02-05 |
| FR1545331A (fr) | 1968-11-08 |
| DE1795724A1 (de) | 1974-02-28 |
| AT281851B (de) | 1970-06-10 |
| NL7409550A (enEXAMPLES) | 1974-09-25 |
| CH512500A (de) | 1971-09-15 |
| BE706861A (fr) | 1968-05-22 |
| SE366985B (enEXAMPLES) | 1974-05-13 |
| DE1695212B2 (de) | 1974-02-14 |
| DE1795724C3 (de) | 1979-05-23 |
| ES347576A1 (es) | 1969-02-01 |
| CA946397A (en) | 1974-04-30 |
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