BE718271A - - Google Patents
Info
- Publication number
- BE718271A BE718271A BE718271DA BE718271A BE 718271 A BE718271 A BE 718271A BE 718271D A BE718271D A BE 718271DA BE 718271 A BE718271 A BE 718271A
- Authority
- BE
- Belgium
- Prior art keywords
- oxime
- preparation
- compound
- ethynyl
- acyl radical
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002513 implantation Methods 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 17
- -1 acyl radical Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 101800000021 N-terminal protease Proteins 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150067355 Est-6 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229940003304 dilt Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE718271 | 1968-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE718271A true BE718271A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1969-01-20 |
Family
ID=3853281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE718271D BE718271A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1968-07-18 | 1968-07-18 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE718271A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2200010A1 (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1972-09-26 | 1974-04-19 | Warner Lambert Co |
-
1968
- 1968-07-18 BE BE718271D patent/BE718271A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2200010A1 (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) * | 1972-09-26 | 1974-04-19 | Warner Lambert Co |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0253500B1 (en) | Acylanilide derivatives | |
| AU658629B2 (en) | Novel isoxazole derivative and salt thereof | |
| JPH06511497A (ja) | フッ素化１７β−置換，４−アザ−５α−アンドロスタン−３−オン誘導体 | |
| Benn | A new mustard oil glucoside synthesis: The synthesis of glucotropaeolin | |
| BE718271A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | ||
| CH407088A (fr) | Procédé de préparation de dérivés des acides 4-halo-3-sulfamoyl-benzoïques | |
| LU81554A1 (de) | Alkylthiophenoxyalkylamines | |
| CA1140110A (fr) | Procede de preparation de nouveaux derives de l'androst-4-ene | |
| US3780073A (en) | 3-oximes of 19-nortestosterone esters | |
| Kissman et al. | The Geometric Isomers of Isobutyrophenone Oxime | |
| BE1001235A4 (fr) | Nouveaux derives azoliques, leur preparation et leur utilisation comme medicaments. | |
| US3629415A (en) | Suppression of reproduction with 3-oxime and 3-oxime esters of 19-nortestosterone | |
| CH621112A5 (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | ||
| US3214446A (en) | 3-(aminoalkoxy)-estra-1, 3, 5(10)-trien-17beta-ol compounds | |
| US3458541A (en) | 13 - alkyl - 17 - (bis(2-hydroxyethyl)amino)-gon-4-en-3-ones,dinitrates | |
| CH513144A (fr) | Procédé de synthèse de stéroïdes | |
| WO2004096829A2 (fr) | Nouveau procede et intermediaires de preparation de composes 19-nor-steroïdes-17-halogenes | |
| US3542922A (en) | 3-alkylsulfenylpropenoic acid ester-substituted steroids | |
| KR800001450B1 (ko) | 1, 3, 5-트리치환 벤젠 유도체의 제조방법 | |
| US2719856A (en) | Steroid ketal | |
| CN103613631B (zh) | 一种合成烯基叠氮孕酮的方法 | |
| CH426781A (fr) | Procédé pour la conversion de composés 1,2,3,4-tétrahydro-anthracènes en des composés 1,2,3,4,4a,5,12,12a-octahydronaphtacènes | |
| BE661226A (fr) | Acides arylacethydroxamiques, amides correspondants et procedes de preparation. | |
| CH637390A5 (en) | Process for the preparation of 4-oxobenzopyran compounds | |
| CH407161A (fr) | Procédé de préparation de nouveaux dérivés de l'acétanilide |