SU906368A3 - Способ получени аминов или их солей в виде рацематов или оптически активных изомеров - Google Patents
Способ получени аминов или их солей в виде рацематов или оптически активных изомеров Download PDFInfo
- Publication number
- SU906368A3 SU906368A3 SU752163123A SU2163123A SU906368A3 SU 906368 A3 SU906368 A3 SU 906368A3 SU 752163123 A SU752163123 A SU 752163123A SU 2163123 A SU2163123 A SU 2163123A SU 906368 A3 SU906368 A3 SU 906368A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen
- ethylamino
- methyl
- propan
- carbamylphenoxy
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 150000001412 amines Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 abstract 6
- DQJFPTCQJBBACG-UHFFFAOYSA-N 4-[2-[[1-(2-hydroxypropoxy)-5-(2-methoxyethyl)cyclohexa-2,4-dien-1-yl]amino]ethoxy]benzamide Chemical compound C(N)(=O)C1=CC=C(OCCNC2(OCC(C)O)CC(=CC=C2)CCOC)C=C1 DQJFPTCQJBBACG-UHFFFAOYSA-N 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 abstract 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- -1 acetylaminomethyl Chemical group 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- XENMLDGAMXHYMH-UHFFFAOYSA-N 2-[(2-prop-2-enylphenoxy)methyl]oxirane Chemical compound C=CCC1=CC=CC=C1OCC1OC1 XENMLDGAMXHYMH-UHFFFAOYSA-N 0.000 description 4
- MHIAMONBYDFGFO-UHFFFAOYSA-N 4-(2-aminoethoxy)benzamide Chemical compound NCCOC1=CC=C(C(N)=O)C=C1 MHIAMONBYDFGFO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 150000003152 propanolamines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- AUWZEXMVEMHCAL-UHFFFAOYSA-N 1-(2-methylphenoxy)propan-2-amine Chemical compound CC(N)COC1=CC=CC=C1C AUWZEXMVEMHCAL-UHFFFAOYSA-N 0.000 description 1
- FOUXAGWNANRBBQ-UHFFFAOYSA-N 1-chloro-4-methyl-2-propoxybenzene Chemical compound CCCOC1=CC(C)=CC=C1Cl FOUXAGWNANRBBQ-UHFFFAOYSA-N 0.000 description 1
- BGOUOFHQLQPABA-UHFFFAOYSA-N 2-[(2,3-dichlorophenoxy)methyl]oxirane Chemical compound ClC1=CC=CC(OCC2OC2)=C1Cl BGOUOFHQLQPABA-UHFFFAOYSA-N 0.000 description 1
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 description 1
- UBZBDHMLUJQMMO-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]-N-phenylacetamide Chemical compound OC(COCC(=O)NC1=CC=CC=C1)CNC(C)C UBZBDHMLUJQMMO-UHFFFAOYSA-N 0.000 description 1
- SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-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
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 150000007513 acids Chemical class 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- BJDFYLUYYXGVFW-UHFFFAOYSA-N bis(2-methylphenyl) 2,3-dihydroxybutanedioate Chemical compound CC1=CC=CC=C1OC(=O)C(O)C(O)C(=O)OC1=CC=CC=C1C BJDFYLUYYXGVFW-UHFFFAOYSA-N 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LZCOQTDXKCNBEE-IKIFYQGPSA-N methscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-IKIFYQGPSA-N 0.000 description 1
- 229960001383 methylscopolamine Drugs 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- HMURKIUWFIQGOI-UHFFFAOYSA-N n-ethoxybenzamide Chemical compound CCONC(=O)C1=CC=CC=C1 HMURKIUWFIQGOI-UHFFFAOYSA-N 0.000 description 1
- UHDKXFCUGVGVDP-UHFFFAOYSA-N n-ethyl-2-hydroxybenzamide Chemical compound CCNC(=O)C1=CC=CC=C1O UHDKXFCUGVGVDP-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
- 229960001749 practolol Drugs 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229950003004 tolamolol Drugs 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/34—Oxygen atoms
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7413789A SE422052B (sv) | 1974-11-01 | 1974-11-01 | Forfarande for framstellning av vissa angivna 1-fenoxi-2-hydroxi-3-aminofenyl-propylderivat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU906368A3 true SU906368A3 (ru) | 1982-02-15 |
Family
ID=20322597
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752163123A SU906368A3 (ru) | 1974-11-01 | 1975-08-08 | Способ получени аминов или их солей в виде рацематов или оптически активных изомеров |
| SU762393516A SU625599A3 (ru) | 1974-11-01 | 1976-09-03 | Способ получени аминов или их солей |
| SU762393515A SU637078A3 (ru) | 1974-11-01 | 1976-09-03 | Способ получени аминов или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762393516A SU625599A3 (ru) | 1974-11-01 | 1976-09-03 | Способ получени аминов или их солей |
| SU762393515A SU637078A3 (ru) | 1974-11-01 | 1976-09-03 | Способ получени аминов или их солей |
Country Status (24)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119718A (en) * | 1977-05-02 | 1978-10-10 | Merck & Co., Inc. | 3-Amino-2-oxy-propoxy-substituted isothiazoles |
| SE7807408L (sv) * | 1978-06-30 | 1979-12-31 | Haessle Ab | Hjertaktiva foreningar |
| DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
| US4410548A (en) * | 1980-07-09 | 1983-10-18 | Reckitt & Colman Products Limited | Propanolamine derivatives |
| DE3125870C2 (de) * | 1980-07-09 | 1994-09-15 | William John Louis | 3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel |
| FR2508032A1 (fr) * | 1981-06-17 | 1982-12-24 | Delalande Sa | Nouveaux derives amino-3 aryloxymethyl-2 propanol-1, leur procede de preparation et leurs applications en therapeutique |
| DE3151201A1 (de) * | 1981-12-23 | 1983-07-28 | Beiersdorf Ag, 2000 Hamburg | Substituierte phenoxyalkanolamine und phenoxyalkanol-cycloalkylamine, verfahren zu ihrer herstellung, diese verbindungen enthaltende pharmazeutische zubereitungen und zwischenprodukte |
| SE457505B (sv) * | 1984-01-10 | 1989-01-09 | Lejus Medical Ab | Laminatbelagd oral farmaceutisk komposition och foerfarande foer dess framstaellning |
| DE3433616A1 (de) * | 1984-08-08 | 1986-02-20 | BBC Aktiengesellschaft Brown, Boveri & Cie., Baden, Aargau | Schutzeinrichtung fuer ein elektrisches netz |
| JPS6341451A (ja) * | 1986-08-06 | 1988-02-22 | Nippon Kayaku Co Ltd | エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 |
| US5321036A (en) * | 1993-02-10 | 1994-06-14 | Bristol-Myers Squibb Company | Thiazole and oxazole-based β3 adrenergic receptor agonists |
-
1974
- 1974-07-02 ZA ZA00754241A patent/ZA754241B/xx unknown
- 1974-11-01 SE SE7413789A patent/SE422052B/xx unknown
-
1975
- 1975-07-02 ZA ZA00754240A patent/ZA754240B/xx unknown
- 1975-07-12 DE DE19752531312 patent/DE2531312A1/de not_active Ceased
- 1975-07-31 FI FI752201A patent/FI752201A7/fi not_active Application Discontinuation
- 1975-07-31 AT AT592975A patent/AT344142B/de not_active IP Right Cessation
- 1975-08-04 AU AU83637/75A patent/AU498770B2/en not_active Expired
- 1975-08-06 NO NO752765A patent/NO144773C/no unknown
- 1975-08-06 NZ NZ178313A patent/NZ178313A/xx unknown
- 1975-08-08 DD DD187775A patent/DD119207A5/xx unknown
- 1975-08-08 SU SU752163123A patent/SU906368A3/ru active
- 1975-08-11 NL NL7509548A patent/NL7509548A/xx not_active Application Discontinuation
- 1975-08-14 IE IE1809/75A patent/IE41652B1/en unknown
- 1975-09-09 GB GB37073/75A patent/GB1524036A/en not_active Expired
- 1975-09-16 CH CH1196775A patent/CH618417A5/de not_active IP Right Cessation
- 1975-10-02 DK DK444475A patent/DK444475A/da unknown
- 1975-10-21 FR FR7532204A patent/FR2289172A1/fr active Granted
- 1975-10-30 CS CS757328A patent/CS189726B2/cs unknown
- 1975-10-30 HU HU75HE694A patent/HU172652B/hu unknown
- 1975-10-31 CA CA238,763A patent/CA1093095A/en not_active Expired
- 1975-10-31 LU LU73703A patent/LU73703A1/xx unknown
- 1975-10-31 BE BE161438A patent/BE835090A/xx unknown
- 1975-10-31 BE BE161439A patent/BE835091A/xx unknown
- 1975-10-31 JP JP50131345A patent/JPS51131839A/ja active Pending
-
1976
- 1976-09-03 SU SU762393516A patent/SU625599A3/ru active
- 1976-09-03 SU SU762393515A patent/SU637078A3/ru active
-
1979
- 1979-08-28 CH CH780979A patent/CH622490A5/de not_active IP Right Cessation
- 1979-08-28 CH CH781079A patent/CH622491A5/de not_active IP Right Cessation
-
1981
- 1981-07-31 HK HK360/81A patent/HK36081A/xx unknown
-
1982
- 1982-12-30 MY MY85/82A patent/MY8200085A/xx unknown
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