CH507240A - Verfahren zur Herstellung von aromatischen Äthern - Google Patents
Verfahren zur Herstellung von aromatischen ÄthernInfo
- Publication number
- CH507240A CH507240A CH239771A CH239771A CH507240A CH 507240 A CH507240 A CH 507240A CH 239771 A CH239771 A CH 239771A CH 239771 A CH239771 A CH 239771A CH 507240 A CH507240 A CH 507240A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- compounds
- dihydro
- compound
- Prior art date
Links
- 150000008378 aryl ethers Chemical class 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 125000004149 thio group Chemical group *S* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 abstract description 3
- 230000003266 anti-allergic effect Effects 0.000 abstract description 3
- 229940124584 antitussives Drugs 0.000 abstract description 3
- 229960001413 acetanilide Drugs 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 239000000043 antiallergic agent Substances 0.000 abstract 1
- 239000003434 antitussive agent Substances 0.000 abstract 1
- 125000005239 aroylamino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- -1 alkoxy radicals Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-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
- 239000005711 Benzoic acid Substances 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- APIYBVUCZRMXKK-UHFFFAOYSA-N N-[4-[3-[4-(4-fluorophenyl)-3,6-dihydro-2H-pyridin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound FC1=CC=C(C=C1)C=1CCN(CC1)CC(COC1=CC=C(NC(C)=O)C=C1)O APIYBVUCZRMXKK-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SSMYTAQHMUHRSK-UHFFFAOYSA-N n-(4-hydroxyphenyl)propanamide Chemical compound CCC(=O)NC1=CC=C(O)C=C1 SSMYTAQHMUHRSK-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nozzles (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239771A CH507240A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239771A CH507240A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH1926868A CH543508A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507240A true CH507240A (de) | 1971-05-15 |
Family
ID=4438412
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239771A CH507240A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH1926868A CH543508A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239471A CH543509A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239571A CH506525A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239671A CH507239A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1926868A CH543508A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239471A CH543509A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239571A CH506525A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
| CH239671A CH507239A (de) | 1968-12-24 | 1968-12-24 | Verfahren zur Herstellung von aromatischen Äthern |
Country Status (19)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960873A (en) * | 1970-05-20 | 1976-06-01 | Sumitomo Chemical Co., Ltd. | 1-Phenylthiopropyl-4-hydroxy-4-phenyl piperidines |
| CH558354A (de) * | 1970-06-17 | 1975-01-31 | Hoffmann La Roche | Verfahren zur herstellung von aromatischen aethern. |
| US3879405A (en) * | 1970-06-19 | 1975-04-22 | Hoffmann La Roche | Tetrahydropyridine derivatives |
| US3951987A (en) * | 1970-06-19 | 1976-04-20 | Hoffmann-La Roche Inc. | Tetrahydropyridine derivatives |
| US3927006A (en) * | 1970-06-19 | 1975-12-16 | Hoffmann La Roche | Tetrahydropyridine derivatives |
| CH547802A (de) * | 1970-06-19 | 1974-04-11 | Hoffmann La Roche | Verfahren zur herstellung von tetrahydropyridinderivaten. |
| SE397088B (sv) * | 1972-06-17 | 1977-10-17 | Sumitomo Chemical Co | Forfarande for framstellning av nya 2-propanolderivat |
| JPS4985074A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-12-22 | 1974-08-15 | ||
| JPS5835195B2 (ja) * | 1974-05-09 | 1983-08-01 | 住友化学工業株式会社 | シンキナフエノキシプロピルアミンユウドウタイノセイホウ |
| US4069221A (en) * | 1975-06-09 | 1978-01-17 | G. D. Searle & Co. | 1-(1-Naphthoxy)-3-(4-substituted-piperidino)-2-propanols |
| DE2632040C2 (de) * | 1976-07-16 | 1983-12-29 | Mengeringhausen, Max, Dipl.-Ing. Dr.-Ing., 8700 Würzburg | Verfahren zur Herstellung einer Verbundbauplatte |
| DE3635350A1 (de) * | 1985-10-17 | 1987-06-25 | Kuepper Geb Kaufmann Inge | Aus platten gebildetes bauelement |
| US5364867A (en) * | 1992-11-30 | 1994-11-15 | Sterling Winthrop Inc. | 4-phenylpiperdine agents for treating cns disorders |
| US5698565A (en) * | 1995-06-09 | 1997-12-16 | Hoffmann-La Roche Inc. | Use of phenoxy-pyridine derivatives |
| WO1997032581A1 (en) * | 1996-03-08 | 1997-09-12 | F. Hoffmann-La Roche Ag | Use of 4-phenyl-3,6-dihydro-2h-pyridyl derivatives as nmda receptor subtype blockers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB856587A (en) * | 1956-04-02 | 1960-12-21 | Sterling Drug Inc | Substituted piperidines |
| US3816434A (en) * | 1966-06-24 | 1974-06-11 | Hoffmann La Roche | 4-(3-(4-phenyl-piperidino)-2-hydroxy-propoxy)-benzophenones |
-
1968
- 1968-12-24 CH CH239771A patent/CH507240A/de not_active IP Right Cessation
- 1968-12-24 CH CH1926868A patent/CH543508A/de not_active IP Right Cessation
- 1968-12-24 CH CH239471A patent/CH543509A/de not_active IP Right Cessation
- 1968-12-24 CH CH239571A patent/CH506525A/de not_active IP Right Cessation
- 1968-12-24 CH CH239671A patent/CH507239A/de not_active IP Right Cessation
-
1969
- 1969-12-04 US US882298A patent/US3674799A/en not_active Expired - Lifetime
- 1969-12-09 IL IL33507A patent/IL33507A/en unknown
- 1969-12-10 CA CA069,470A patent/CA969963A/en not_active Expired
- 1969-12-16 GB GB1264564D patent/GB1264564A/en not_active Expired
- 1969-12-18 PH PH10993*UA patent/PH9402A/en unknown
- 1969-12-19 BR BR215344/69A patent/BR6915344D0/pt unknown
- 1969-12-22 DK DK680669AA patent/DK133335B/da unknown
- 1969-12-22 IE IE1695/69A patent/IE33890B1/xx unknown
- 1969-12-22 BE BE743493D patent/BE743493A/xx unknown
- 1969-12-22 FI FI693714A patent/FI52338C/fi active
- 1969-12-22 IE IE1694/69A patent/IE33981B1/xx unknown
- 1969-12-23 AT AT1199369A patent/AT295534B/de not_active IP Right Cessation
- 1969-12-23 NL NL6919281A patent/NL6919281A/xx not_active Application Discontinuation
- 1969-12-23 DE DE19691964421 patent/DE1964421A1/de active Pending
- 1969-12-23 AT AT192071A patent/AT295536B/de not_active IP Right Cessation
- 1969-12-23 SE SE17877/69A patent/SE357363B/xx unknown
- 1969-12-23 ES ES374837A patent/ES374837A1/es not_active Expired
- 1969-12-23 NO NO695110A patent/NO132196C/no unknown
- 1969-12-23 FR FR6944583A patent/FR2027037B1/fr not_active Expired
- 1969-12-24 JP JP44104209A patent/JPS4931991B1/ja active Pending
-
1973
- 1973-10-03 US US403133A patent/US3859294A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60030883T2 (de) | Verfahren zur herstellung von alfentanil, sufentanil und remifentanil | |
| CH507240A (de) | Verfahren zur Herstellung von aromatischen Äthern | |
| CH616923A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH506536A (de) | Verfahren zur Herstellung von aromatischen Äthern | |
| DE3026201A1 (de) | Aminoaetheroxide, verfahren zu ihrer herstellung sowie ihre therapeutische verwendung | |
| DE2311570C2 (de) | 4-Aminochinoline, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| DE1643296A1 (de) | Mittel zur Behandlung bronchospastischer Erscheinungen | |
| DE2828529A1 (de) | Neue 5-phenylpyrazol-derivate, verfahren zu deren herstellung und arzneimittel | |
| DE1593579B1 (de) | Hydroxy-cyclohexylamine,deren physiologisch vertraeglichen Saeureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE68903263T2 (de) | Substituierte aromatische verbindungen mit zentraler nervensystem-wirkung. | |
| DE3209304C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2461069A1 (de) | Neue cholesterinsenkende verbindungen | |
| DE2257639A1 (de) | Neue ester und aether von ketoximen, verfahren zu deren herstellung sowie diese verbindungen enthaltende therapeutische zubereitungen | |
| DD150060A5 (de) | Verfahren zur herstellung von neuen phenthiazin-derivaten | |
| DE936747C (de) | Verfahren zur Herstellung von neuen Pyrimidinderivaten und deren Salzen | |
| DE2551355A1 (de) | N-benzylpiperazine | |
| AT226710B (de) | Verfahren zur Herstellung von neuen Dihydrochinoxalonen-(2) und von deren Salzen | |
| DE1901167C3 (de) | Substituierte Indole, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE1593579C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| AT335458B (de) | Verfahren zur herstellung von neuen 2-substituierten 1,2,3,4,6,7,12,12a-octahydropyrazino-(2',1':6,1)-pyrido-(3,4-b)-indolen und ihren salzen | |
| DE1018869B (de) | Verfahren zur Herstellung von Aminoalkylpurinderivaten | |
| DE2500692C3 (de) | Derivate des 4-Amidoalkylen-4'oxy diphenyle | |
| DE2015731C3 (de) | Azamorphinanverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen | |
| AT334905B (de) | Verfahren zur herstellung neuer piperazin-derivate und ihrer salze | |
| DE1445059A1 (de) | Verfahren zur Herstellung von neuen pharmakologisch wertvollen Carbostyrilderivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |