BE513932A - - Google Patents
Info
- Publication number
- BE513932A BE513932A BE513932DA BE513932A BE 513932 A BE513932 A BE 513932A BE 513932D A BE513932D A BE 513932DA BE 513932 A BE513932 A BE 513932A
- Authority
- BE
- Belgium
- Prior art keywords
- amino
- nitro
- sep
- ethyl
- tertiary
- Prior art date
Links
- -1 benzoyl halide Chemical class 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004429 atoms Chemical group 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 16
- 239000000155 melt Substances 0.000 description 15
- 239000012256 powdered iron Substances 0.000 description 15
- 150000007970 thio esters Chemical class 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- DJDAPLBWGIXUAG-UHFFFAOYSA-N 2-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(Cl)=O DJDAPLBWGIXUAG-UHFFFAOYSA-N 0.000 description 2
- QCXXLRLARBGKRU-UHFFFAOYSA-N NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OC Chemical compound NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OC QCXXLRLARBGKRU-UHFFFAOYSA-N 0.000 description 2
- XKLZRSVDPAVQHN-UHFFFAOYSA-N NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCC Chemical compound NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCC XKLZRSVDPAVQHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NRMCREZNMBFXNA-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCCCCCC Chemical compound [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCCCCCC NRMCREZNMBFXNA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000003638 reducing agent Substances 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical compound CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 description 1
- QYTUGWTXRWZBHH-UHFFFAOYSA-N 2-butoxy-4-nitrobenzoic acid Chemical compound CCCCOC1=CC([N+]([O-])=O)=CC=C1C(O)=O QYTUGWTXRWZBHH-UHFFFAOYSA-N 0.000 description 1
- KRTGGWTUBIWIHD-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1-thiol Chemical compound SCCCN1CCCCC1 KRTGGWTUBIWIHD-UHFFFAOYSA-N 0.000 description 1
- 229940095564 Anhydrous Calcium Sulfate Drugs 0.000 description 1
- 210000000988 Bone and Bones Anatomy 0.000 description 1
- UALKDWOZSUGYCC-UHFFFAOYSA-M C(C)N(CCC1C(SC=C1[N+](=O)[O-])(C1=CC=CC=C1C(=O)[O-])OCC)CC Chemical compound C(C)N(CCC1C(SC=C1[N+](=O)[O-])(C1=CC=CC=C1C(=O)[O-])OCC)CC UALKDWOZSUGYCC-UHFFFAOYSA-M 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 101700043519 ERI1 Proteins 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 229910003944 H3 PO4 Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 229960005015 Local anesthetics Drugs 0.000 description 1
- 229940083877 Local anesthetics for treatment of hemorrhoids and anal fissures for topical use Drugs 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N Molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- QQZBXEIFPSBSDR-UHFFFAOYSA-N NC=1CC(SC1)(C1=CC=CC=C1C(=O)OC(C)CN(C)C)OCCCC Chemical compound NC=1CC(SC1)(C1=CC=CC=C1C(=O)OC(C)CN(C)C)OCCCC QQZBXEIFPSBSDR-UHFFFAOYSA-N 0.000 description 1
- HAAJNIDOKSIIRG-UHFFFAOYSA-N NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OC Chemical compound NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OC HAAJNIDOKSIIRG-UHFFFAOYSA-N 0.000 description 1
- ZWHKAQYIYWCQTL-UHFFFAOYSA-N NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCCCCCC Chemical compound NC=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCCCCCC ZWHKAQYIYWCQTL-UHFFFAOYSA-N 0.000 description 1
- GHCBEQILVGRUGA-UHFFFAOYSA-N NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCC)OCCC Chemical compound NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCC)OCCC GHCBEQILVGRUGA-UHFFFAOYSA-N 0.000 description 1
- JYUFDIPLNBNZJN-UHFFFAOYSA-N NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCC Chemical compound NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCC JYUFDIPLNBNZJN-UHFFFAOYSA-N 0.000 description 1
- MACSWEUWMCPZSQ-UHFFFAOYSA-N NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCCC Chemical compound NC=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCCC MACSWEUWMCPZSQ-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- JUDWVRWAVZZPAZ-UHFFFAOYSA-M [N+](=O)([O-])C1C(SC=C1)(C1=CC=CC=C1C(=O)[O-])OCCCC Chemical compound [N+](=O)([O-])C1C(SC=C1)(C1=CC=CC=C1C(=O)[O-])OCCCC JUDWVRWAVZZPAZ-UHFFFAOYSA-M 0.000 description 1
- FSCVZTJMTPKBRV-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCC Chemical compound [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCCN(CC)CC)OCC FSCVZTJMTPKBRV-UHFFFAOYSA-N 0.000 description 1
- PGPVBNIXGYMGNG-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OC Chemical compound [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OC PGPVBNIXGYMGNG-UHFFFAOYSA-N 0.000 description 1
- WOVADGMLTPEBAI-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCC Chemical compound [N+](=O)([O-])C=1CC(SC1)(C1=CC=CC=C1C(=O)OCCN(CC)CC)OCC WOVADGMLTPEBAI-UHFFFAOYSA-N 0.000 description 1
- XUTWGXRIMLUSFS-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OC(C)CN(C)C)OCCCC Chemical compound [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OC(C)CN(C)C)OCCCC XUTWGXRIMLUSFS-UHFFFAOYSA-N 0.000 description 1
- CXKCPZDMTZUWCU-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCCN(C)C)OCCCC Chemical compound [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCCN(C)C)OCCCC CXKCPZDMTZUWCU-UHFFFAOYSA-N 0.000 description 1
- HWTYIHFKLPTDQK-UHFFFAOYSA-N [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCCN(CC)CC)OC Chemical compound [N+](=O)([O-])C=1CC(SC=1)(C1=CC=CC=C1C(=O)OCCCCN(CC)CC)OC HWTYIHFKLPTDQK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- PHENPABYBHPABM-UHFFFAOYSA-N acetic acid;octane Chemical compound CC(O)=O.CCCCCCCC PHENPABYBHPABM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 230000003522 irritant Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229940064003 local anesthetic throat preparations Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
- 230000003472 neutralizing Effects 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atoms Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- VRRFSFYSLSPWQY-UHFFFAOYSA-N sulfanylidenecobalt Chemical compound [Co]=S VRRFSFYSLSPWQY-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE513932A true BE513932A (zh) |
Family
ID=151898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE513932D BE513932A (zh) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE513932A (zh) |
-
0
- BE BE513932D patent/BE513932A/fr unknown
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