DD149063A5 - Verfahren zur herstellung von p-chloracetophenonoximderivaten - Google Patents
Verfahren zur herstellung von p-chloracetophenonoximderivaten Download PDFInfo
- Publication number
- DD149063A5 DD149063A5 DD80218997A DD21899780A DD149063A5 DD 149063 A5 DD149063 A5 DD 149063A5 DD 80218997 A DD80218997 A DD 80218997A DD 21899780 A DD21899780 A DD 21899780A DD 149063 A5 DD149063 A5 DD 149063A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- preparation
- general formula
- compounds
- oxime
- nitrogen atom
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 15
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- KAXTWDXRCMICEQ-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethylidene]hydroxylamine Chemical class ON=C(C)C1=CC=C(Cl)C=C1 KAXTWDXRCMICEQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 20
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 13
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 10
- 230000000954 anitussive effect Effects 0.000 abstract description 8
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 6
- 239000002221 antipyretic Substances 0.000 abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 238000001356 surgical procedure Methods 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 13
- 239000003814 drug Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 206010011224 Cough Diseases 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- ZEWPZWZBVHCPOR-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethylideneamino]oxy-n,n-dimethylethanamine Chemical compound CN(C)CCON=C(C)C1=CC=C(Cl)C=C1 ZEWPZWZBVHCPOR-UHFFFAOYSA-N 0.000 description 2
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical class NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GBRXONPWVDUSSR-PXJKFVASSA-N (z)-1-(4-chlorophenyl)-n-(2-morpholin-4-ylethoxy)ethanimine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C(/C)=N\OCCN1CCOCC1 GBRXONPWVDUSSR-PXJKFVASSA-N 0.000 description 1
- JMLYGCHTFNQUPP-VSORCOHTSA-N (z)-1-(4-chlorophenyl)-n-(2-piperidin-1-ylethoxy)ethanimine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C(/C)=N\OCCN1CCCCC1 JMLYGCHTFNQUPP-VSORCOHTSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- UGPLUORMBKEGNT-PXJKFVASSA-N 2-[(z)-1-(4-chlorophenyl)ethylideneamino]oxy-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCO\N=C(\C)C1=CC=C(Cl)C=C1 UGPLUORMBKEGNT-PXJKFVASSA-N 0.000 description 1
- 244000171897 Acacia nilotica subsp nilotica Species 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 102100040141 Aminopeptidase O Human genes 0.000 description 1
- 108050008333 Aminopeptidase O Proteins 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- QQKYFCAJVVQWPC-UHFFFAOYSA-N Cl.[B] Chemical compound Cl.[B] QQKYFCAJVVQWPC-UHFFFAOYSA-N 0.000 description 1
- 101000804902 Drosophila melanogaster Xaa-Pro aminopeptidase ApepP Proteins 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241001539019 Monolene Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- ZEHGKSPCAMLJDC-UHFFFAOYSA-M acetylcholine bromide Chemical compound [Br-].CC(=O)OCC[N+](C)(C)C ZEHGKSPCAMLJDC-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7903617A FR2449081A1 (fr) | 1979-02-13 | 1979-02-13 | Nouveaux derives de p-chloroacetophenone oxime, leur preparation et leur application en tant que medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149063A5 true DD149063A5 (de) | 1981-06-24 |
Family
ID=9221905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80218997A DD149063A5 (de) | 1979-02-13 | 1980-02-11 | Verfahren zur herstellung von p-chloracetophenonoximderivaten |
Country Status (25)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2435830A (en) * | 2006-03-09 | 2007-09-12 | Del Dr Esteve S A Spain Lab | Oxime ether compounds for the treatment of conditions associated with food uptake |
| JP4936905B2 (ja) * | 2007-01-10 | 2012-05-23 | 株式会社リコー | プロセスカートリッジ及び画像形成装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3692835A (en) * | 1967-04-05 | 1972-09-19 | Jan Van Dijk | Pharmacologically active amino-ethyl oximes |
| BE754448A (fr) * | 1969-08-08 | 1971-02-05 | Choay Sa | Nouveaux medicaments a base d'imines substituees, nouvelles imines substituees et leurs procedes de fabrication |
-
1979
- 1979-02-13 FR FR7903617A patent/FR2449081A1/fr active Granted
-
1980
- 1980-01-24 ES ES487971A patent/ES487971A1/es not_active Expired
- 1980-02-05 IL IL59315A patent/IL59315A/xx unknown
- 1980-02-05 AT AT0062380A patent/AT369730B/de not_active IP Right Cessation
- 1980-02-06 PT PT70792A patent/PT70792A/pt not_active IP Right Cessation
- 1980-02-06 PL PL22184080A patent/PL221840A1/xx unknown
- 1980-02-06 US US06/119,104 patent/US4342763A/en not_active Expired - Lifetime
- 1980-02-07 BE BE0/199297A patent/BE881589A/fr not_active IP Right Cessation
- 1980-02-07 GB GB8004154A patent/GB2043063B/en not_active Expired
- 1980-02-07 CA CA000345342A patent/CA1140127A/fr not_active Expired
- 1980-02-07 AR AR279900A patent/AR222522A1/es active
- 1980-02-08 GR GR61169A patent/GR65624B/el unknown
- 1980-02-08 CH CH101880A patent/CH644098A5/fr not_active IP Right Cessation
- 1980-02-08 YU YU334/80A patent/YU41502B/xx unknown
- 1980-02-09 EG EG72/80A patent/EG14161A/xx active
- 1980-02-11 RO RO80100151A patent/RO77526A/ro unknown
- 1980-02-11 BG BG046561A patent/BG34034A3/xx unknown
- 1980-02-11 DE DE3004972A patent/DE3004972C2/de not_active Expired
- 1980-02-11 FI FI800413A patent/FI71136C/fi not_active IP Right Cessation
- 1980-02-11 DD DD80218997A patent/DD149063A5/de unknown
- 1980-02-12 SE SE8001073A patent/SE447246B/sv not_active IP Right Cessation
- 1980-02-12 HU HU80312A patent/HU183057B/hu not_active IP Right Cessation
- 1980-02-12 NL NLAANVRAGE8000880,A patent/NL187974C/xx not_active IP Right Cessation
- 1980-02-12 SE SE8001073D patent/SE8001073L/xx not_active Application Discontinuation
- 1980-02-12 CS CS80939A patent/CS216651B2/cs unknown
- 1980-02-13 JP JP55016494A patent/JPS5849539B2/ja not_active Expired
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