BE621721A - - Google Patents
Info
- Publication number
- BE621721A BE621721A BE621721DA BE621721A BE 621721 A BE621721 A BE 621721A BE 621721D A BE621721D A BE 621721DA BE 621721 A BE621721 A BE 621721A
- Authority
- BE
- Belgium
- Prior art keywords
- derivative
- lower alkyl
- radical
- monocyclic
- ketones
- Prior art date
Links
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229960003387 progesterone Drugs 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- 239000000186 progesterone Substances 0.000 claims description 7
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- -1 monocyclic aromatic aldehydes Chemical class 0.000 description 13
- 150000002576 ketones Chemical class 0.000 description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000003935 benzaldehydes Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical class OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WRJZDDJYWWJLIS-UHFFFAOYSA-N 4-methyl-1-phenylpentan-1-one Chemical compound CC(C)CCC(=O)C1=CC=CC=C1 WRJZDDJYWWJLIS-UHFFFAOYSA-N 0.000 description 1
- DGMYRPFYNFQCHM-UHFFFAOYSA-N 5-phenylpentan-2-one Chemical class CC(=O)CCCC1=CC=CC=C1 DGMYRPFYNFQCHM-UHFFFAOYSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE621721A true BE621721A (d) |
Family
ID=194623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE621721D BE621721A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE621721A (d) |
-
0
- BE BE621721D patent/BE621721A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0109317B1 (fr) | Dérivés de phényl-1 pipéridino-2 propanol, leur préparation, et médicaments qui les contiennent | |
| EP0877607B1 (fr) | Composes biphenyles et leur utilisation comme agents estrogeniques | |
| CH616161A5 (d) | ||
| CA2021250A1 (fr) | Medicaments a base de derives de 1h-benzoxadiazine-4, 1, 2, nouveaux derives et leurs procedes de preparation | |
| EP0172083B1 (fr) | Nouveaux amides substitués, leur préparation et les médicaments qui les contiennent | |
| EP0310484A1 (fr) | Dérivés d'alcadienes, leurs préparations, les médicaments les contenant et produits intermédiaires | |
| EP0729933A1 (fr) | Dérivés tricycliques, leur préparation et leur application à la préparation de la colchicine et de la thiocolchicine optiquement actives ou racémiques et d'analogues ou dérivés et intermédiaires | |
| BE621721A (d) | ||
| EP0395528A2 (fr) | Dérivés du 4-phénylméthyl 1H-indole, procédé et intermédiaires de préparation, application à titre de médicaments et compositions les renfermant. | |
| EP0443957B1 (fr) | Nouveaux produits stéroides comportant un radical spiro en position 17, leur procédé de préparation et les intermédiaires de ce procédé, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant | |
| EP0955286A1 (fr) | Dérivés du dihydro ou tétrahydronaphtalène ayant une activité (anti-)oestrogène | |
| LU81497A1 (fr) | Nouveaux derives acetyleniques de l'androst-4-ene,leur procede de preparation,leur application comme medicament et les compositions pharmaceutiques les renfermant | |
| EP0044575B1 (fr) | Produits intermédiaires dans la synthèse de 19-nor stéroides substitués en position 2 | |
| WO1992021665A1 (fr) | Nouveaux derives de l'oxazole et leur preparation | |
| EP0059146B1 (fr) | Nouveaux médicaments dérivés de la 3-hydroxy dodécahydro benz (e) inden-7-one, produits dérivés de la 3-hydroxy dodécahydro benz (e) inden-7-one et leur procédé de préparation | |
| WO1992021664A1 (fr) | Nouveaux derives de l'oxazole, leur preparation et les compositions qui les contiennent | |
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| EP0017523B1 (fr) | Nouveaux dérivés du dithiépinno (1,4)(2,3-c)pyrrole, leur préparation et les médicaments qui les contiennent | |
| EP0076713B1 (fr) | Nouveaux dérivés de l'aminométhyl 1H-indole 4-méthanol et leurs sels, leur procédé et les intermédiaires de préparation, leur application à titre de médicaments, les compositions les renfermant | |
| BE884977A (fr) | Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes | |
| EP0194945B1 (fr) | Nouveaux dérivés de l'acide thiophène acétique, leur procédé de préparation, les intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant | |
| CH633714A5 (fr) | Derives 17alpha-acetyleniques de l'androst 4-ene, procede de prepararation et compositions pharmaceutiques. | |
| EP0403318A1 (fr) | Procédé de préparation d'une nouvelle substance antitumorale, l'amino-3 (amino-2 1H-imidazolyl-4-)-1 chloro-2 propanol-1 et de ses sels sous forme racémique thréo, utilisable comme médicament | |
| FR2745291A1 (fr) | Procede industriel de fabrication de trenbolone | |
| EP0000009B1 (fr) | Procédé d'oxydation de quinine en quininone et quinidinone. |