DE2163000C3 - (Piperidin-4-spiro)-5-oxazolidone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen - Google Patents
(Piperidin-4-spiro)-5-oxazolidone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische ZubereitungenInfo
- Publication number
- DE2163000C3 DE2163000C3 DE19712163000 DE2163000A DE2163000C3 DE 2163000 C3 DE2163000 C3 DE 2163000C3 DE 19712163000 DE19712163000 DE 19712163000 DE 2163000 A DE2163000 A DE 2163000A DE 2163000 C3 DE2163000 C3 DE 2163000C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- spiro
- oxazolidone
- preparation
- piperidin
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title description 25
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 alkyl ketone Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000001105 femoral artery Anatomy 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FVNFBBAOMBJTST-UHFFFAOYSA-N 8-(2-phenylethyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound O1C(=O)NCC11CCN(CCC=2C=CC=CC=2)CC1 FVNFBBAOMBJTST-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 101000687905 Homo sapiens Transcription factor SOX-2 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102100024270 Transcription factor SOX-2 Human genes 0.000 description 1
- 208000012886 Vertigo Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960002912 fenspiride Drugs 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007937 lozenge Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 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
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6043070A GB1377610A (en) | 1970-12-19 | 1970-12-19 | 5-piperidine-4-spiro- oxazolidinones method for their preparation and applications thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2163000A1 DE2163000A1 (de) | 1972-06-29 |
| DE2163000B2 DE2163000B2 (de) | 1978-04-13 |
| DE2163000C3 true DE2163000C3 (de) | 1978-12-14 |
Family
ID=10485592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163000 Expired DE2163000C3 (de) | 1970-12-19 | 1971-12-18 | (Piperidin-4-spiro)-5-oxazolidone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5538356B1 (enExample) |
| BE (1) | BE775984A (enExample) |
| CH (1) | CH546255A (enExample) |
| DE (1) | DE2163000C3 (enExample) |
| ES (1) | ES398106A1 (enExample) |
| FR (1) | FR2117894B1 (enExample) |
| GB (1) | GB1377610A (enExample) |
| SE (1) | SE370401B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244961A (en) | 1978-10-26 | 1981-01-13 | Syntex (U.S.A.) Inc. | 1-Oxa-3,8-diazaspiro[4.5]decan-2-ones antihypertensive agents |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1478932A (en) * | 1975-03-06 | 1977-07-06 | Science Union & Cie | 8-(3-chromanyl)-1-oxa-3,8-diazaspiro(4,5)decan-2-ones and thiones |
| ES8401072A1 (es) * | 1982-11-23 | 1983-12-16 | Faes | Procedimiento de preparacion de un nuevo espirodecano. |
| FR2615515B1 (fr) * | 1987-05-22 | 1989-06-30 | Adir | Nouveaux derives du spiro 4, 5 decane, leur procede de preparation et les compositions pharmaceutiques les renfermant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2035780A1 (enExample) * | 1969-03-25 | 1970-12-24 | Logeais Labor Jacques |
-
1970
- 1970-12-19 GB GB6043070A patent/GB1377610A/en not_active Expired
-
1971
- 1971-11-29 BE BE775984A patent/BE775984A/xx not_active IP Right Cessation
- 1971-12-01 CH CH546255D patent/CH546255A/fr not_active IP Right Cessation
- 1971-12-02 FR FR7143246A patent/FR2117894B1/fr not_active Expired
- 1971-12-16 SE SE1612271A patent/SE370401B/xx unknown
- 1971-12-17 JP JP10253571A patent/JPS5538356B1/ja active Pending
- 1971-12-18 DE DE19712163000 patent/DE2163000C3/de not_active Expired
- 1971-12-18 ES ES398106A patent/ES398106A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244961A (en) | 1978-10-26 | 1981-01-13 | Syntex (U.S.A.) Inc. | 1-Oxa-3,8-diazaspiro[4.5]decan-2-ones antihypertensive agents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2117894B1 (enExample) | 1975-06-13 |
| GB1377610A (en) | 1974-12-18 |
| CH546255A (fr) | 1974-02-28 |
| BE775984A (fr) | 1972-03-16 |
| ES398106A1 (es) | 1974-07-01 |
| SE370401B (enExample) | 1974-10-14 |
| DE2163000A1 (de) | 1972-06-29 |
| FR2117894A1 (enExample) | 1972-07-28 |
| DE2163000B2 (de) | 1978-04-13 |
| JPS5538356B1 (enExample) | 1980-10-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1957706C3 (de) | Kernsubstituierte 3-Phenoxy-l-phenoxyalkylamino-propan-2-ole und Arzneimittel auf deren Basis | |
| DE2500110A1 (de) | 3-aryloxy-3-phenylpropylamine und verfahren zu ihrer herstellung | |
| DE2310918B2 (de) | 3-lsobutoxy-2-pyrrolidino-N-phenyl-N-benzylpropylamin, dessen Salze, Verfahren zu deren Herstellung und Arzneimittel | |
| DE1643262B2 (de) | l-Phenoxy^-hydroxy-S-alklyaminopropane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2830884C2 (enExample) | ||
| CH372667A (de) | Verfahren zur Herstellung von 3-Aryl-3-pyrrolidinolen | |
| DE2631885C2 (de) | 1-(4-Phenoxyphenyl)-piperazin-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| DE1695756B2 (de) | 3,1-benzoxazin-2-one, verfahren zu deren herstellung und arzneimittel | |
| DE2635961A1 (de) | Therapeutisch wirksame verbindungen und verfahren zu ihrer herstellung | |
| DE60019622T2 (de) | Nitroimidazolderivate und diese enthaltende diagnostische bilderzeugungsmittel | |
| DE2163000C3 (de) | (Piperidin-4-spiro)-5-oxazolidone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen | |
| DE2164637B2 (de) | N-(phenoxyalkyl)-alpha-methylphenaethyl-amine bzw. -aminole, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen | |
| DE2717001A1 (de) | Arzneimittel mit antithrombotischer wirkung | |
| DE2130480A1 (de) | Benzofuranderivate und diese enthaltende pharmazeutische Praeparate | |
| DE2062055C3 (de) | Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE3650311T2 (de) | Verwendung von Quinazolinen zur Herstellung eines Arzneimittels zur Behandlung und Vorbeugung von Arrhythmie. | |
| DE2636866A1 (de) | Neue phenothiazinderivate und deren herstellung | |
| DE2844595A1 (de) | Acylaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2235406B2 (de) | 2-Amino-4H-pyrane, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2824066A1 (de) | Neue, zur ulcusbehandlung brauchbare verbindungen, verfahren zu deren herstellung, arzneimittel und zwischenprodukte | |
| DE2023829C3 (de) | Kernsubstituierte 3-Phenoxy-lphenoxyalkyl-amino-propan-2-oIe, Verfahren zu ihrer Herstellung sowie Arzneimittel | |
| DE3107599C2 (de) | N-Cyan-N'-methyl-N"-{2-[(5-methylthio-imidazol-4-yl)-methylthio]-äthyl}-guanidin, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel | |
| DE2942065A1 (de) | Neue 1,6-naphthyridinderivate, verfahren zu ihrer herstellung sowie mittel gegen schwindel und zur verbesserung der zerebralen zirkulation, die diese derivate enthalten | |
| DE2166662A1 (de) | Tricyclische derivate von aliphatischen omega-alkoholen und verfahren zu ihrer herstellung | |
| DE10131217A1 (de) | 3-Phenyl-3,7-diazabicyclo 3,3,1 nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |