FR2474499A2 - Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent - Google Patents
Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent Download PDFInfo
- Publication number
- FR2474499A2 FR2474499A2 FR8001499A FR8001499A FR2474499A2 FR 2474499 A2 FR2474499 A2 FR 2474499A2 FR 8001499 A FR8001499 A FR 8001499A FR 8001499 A FR8001499 A FR 8001499A FR 2474499 A2 FR2474499 A2 FR 2474499A2
- Authority
- FR
- France
- Prior art keywords
- thio
- general formula
- pyridyl
- amine
- antiulcer
- 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.)
- Granted
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title abstract description 6
- 230000000767 anti-ulcer Effects 0.000 title abstract description 3
- 239000003699 antiulcer agent Substances 0.000 title abstract 2
- 239000002731 stomach secretion inhibitor Substances 0.000 title abstract 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title 2
- 239000012988 Dithioester Substances 0.000 claims abstract description 4
- 125000005022 dithioester group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 241000699670 Mus sp. Species 0.000 abstract description 2
- 231100000816 toxic dose Toxicity 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001979 organolithium group Chemical group 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- 150000003222 pyridines Chemical class 0.000 description 5
- -1 sodium hydroxide Chemical class 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 125000005905 mesyloxy group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MCWOUJHWVBNJMS-UHFFFAOYSA-N methyl thiolane-2-carbodithioate Chemical compound S1C(CCC1)C(=S)SC MCWOUJHWVBNJMS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8001499A FR2474499A2 (fr) | 1980-01-24 | 1980-01-24 | Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
| IE620/80A IE49570B1 (en) | 1979-03-30 | 1980-03-20 | 2-(pyrid-2-yl)tetrahydrothiophene derivatives |
| NL8001687A NL8001687A (nl) | 1979-03-30 | 1980-03-21 | Nieuwe 2-(pyridyl-2).tetrahydrothiofeenderivaten, de bereiding ervan alsmede farmaceutische preparaten die de nieuwe derivaten bevatten. |
| US06/134,311 US4272534A (en) | 1979-03-30 | 1980-03-26 | 2-(Pyrid-2-yl)tetrahydrothiophene derivatives |
| NZ193268A NZ193268A (en) | 1979-03-30 | 1980-03-26 | 2-(pyrid-2-yl)-tetrahydrothiophene derivatives and pharmaceutical compositions |
| AU56847/80A AU532337B2 (en) | 1979-03-30 | 1980-03-26 | 2-(pyrid-2-yl) tetrahydrothiophene derivatives |
| GB8010133A GB2046265B (en) | 1979-03-30 | 1980-03-26 | 2-(pyrid-2-yl)tetrahydrothiophene derivatives |
| IL59719A IL59719A (en) | 1979-03-30 | 1980-03-26 | 2-(pyrid-2-yl)tetrahydrothiophene derivatives,process for their preparation and pharmaceutical compositions comprising the same |
| PH23816A PH14804A (en) | 1979-03-30 | 1980-03-26 | Nouveaux derives du(pyridy 1-2)-2 tetrahydrothiophene,leur preparation et les medicaments qui les contiennent |
| SU802899103A SU1048984A3 (ru) | 1980-01-24 | 1980-03-27 | Способ получени производных 2-/2-пиридил/-тетрагидротиофена или их солей |
| AT171480A AT370101B (de) | 1980-01-24 | 1980-03-28 | Verfahren zur herstellung neuer derivate des 2-(pyridyl-2)-tetrahydrothiophens sowie ihrer existenten salze |
| SE8002426A SE8002426L (sv) | 1979-03-30 | 1980-03-28 | Nya derivat av 2-(2-pyridyl)tetrahydrotiofen |
| GR61565A GR67614B (enExample) | 1979-03-30 | 1980-03-28 | |
| PT198071026A PT71026A (en) | 1979-03-30 | 1980-03-28 | Process for preparing of new derivatives (pyridil-2)-2 tetrahidrothiofene |
| LU82307A LU82307A1 (fr) | 1979-03-30 | 1980-03-28 | Nouveaux derives du (pyridy1-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
| CH247380A CH644858A5 (fr) | 1979-03-30 | 1980-03-28 | Derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent. |
| NO800910A NO153055C (no) | 1979-03-30 | 1980-03-28 | Analogifremgangsmaate for fremstilling av terapeutisk aktive nye derivater av 2-(2-pyridyl)tetrahydrotiofen |
| CA000348680A CA1134361A (fr) | 1979-03-30 | 1980-03-28 | Derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
| ES490061A ES490061A0 (es) | 1979-03-30 | 1980-03-28 | Procedimiento para preparar nuevos derivados de (piridil-2)-2-tetrahidrotiofeno |
| DK135480A DK135480A (da) | 1979-03-30 | 1980-03-28 | Fremgangsmaade til fremstilling af 2-(2-pyridyl)-tetrahydrothiopen-derivater |
| FI800971A FI66862C (fi) | 1979-03-30 | 1980-03-28 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 2-(pyridyl-2)-tetrahydrotiofenderivat |
| DE3012142A DE3012142C2 (de) | 1979-03-30 | 1980-03-28 | Neue Derivate des 2-[Pyridyl(2)Jtetrahydrothiophens, ihre Herstellung und die sie enthaltenden Arzneimittel |
| IT21029/80A IT1193524B (it) | 1979-03-30 | 1980-03-28 | Derivati del (piridil-2)-2 tetraidrotiofene,loro preparazione,e medicamenti che li contengono |
| HU80739A HU187273B (en) | 1979-03-30 | 1980-03-28 | Process for preparing new 2-/2-pyridyl/-tetrahydro-thiophene derivatives |
| CS224480A CS228505B2 (en) | 1980-01-24 | 1980-03-31 | Method for the production of new 2-/2-pyridyl/tetrahydrothiophene derivates |
| ES493554A ES8105979A1 (es) | 1980-01-24 | 1980-07-21 | Procedimiento para preparar nuevos derivados de (piridil-2)-2 tetrahidrotiofeno |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8001499A FR2474499A2 (fr) | 1980-01-24 | 1980-01-24 | Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2474499A2 true FR2474499A2 (fr) | 1981-07-31 |
| FR2474499B2 FR2474499B2 (enExample) | 1983-01-28 |
Family
ID=9237823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8001499A Granted FR2474499A2 (fr) | 1979-03-30 | 1980-01-24 | Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2474499A2 (enExample) |
-
1980
- 1980-01-24 FR FR8001499A patent/FR2474499A2/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| EXBK/55 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2474499B2 (enExample) | 1983-01-28 |
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