BE631558A - - Google Patents
Info
- Publication number
- BE631558A BE631558A BE631558DA BE631558A BE 631558 A BE631558 A BE 631558A BE 631558D A BE631558D A BE 631558DA BE 631558 A BE631558 A BE 631558A
- Authority
- BE
- Belgium
- Prior art keywords
- radical
- dihydro
- formula
- derivative
- acid
- Prior art date
Links
- 150000003254 radicals Chemical class 0.000 claims 35
- 239000002253 acid Substances 0.000 claims 29
- 239000000243 solution Substances 0.000 claims 25
- 229910052751 metal Inorganic materials 0.000 claims 24
- 239000002184 metal Substances 0.000 claims 24
- -1 alkyl radical Chemical group 0.000 claims 23
- 238000002360 preparation method Methods 0.000 claims 22
- 239000000047 product Substances 0.000 claims 22
- 230000000875 corresponding Effects 0.000 claims 21
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 14
- 238000002844 melting Methods 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 13
- 150000001412 amines Chemical class 0.000 claims 12
- 229910052783 alkali metal Inorganic materials 0.000 claims 10
- 150000001340 alkali metals Chemical class 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 150000004820 halides Chemical class 0.000 claims 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 10
- 150000002148 esters Chemical class 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 8
- 239000000155 melt Substances 0.000 claims 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 6
- 150000002829 nitrogen Chemical group 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- DOBRDRYODQBAMW-UHFFFAOYSA-N Copper(I) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 238000010992 reflux Methods 0.000 claims 5
- 239000000725 suspension Substances 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atoms Chemical group 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 238000001704 evaporation Methods 0.000 claims 4
- 238000005658 halogenation reaction Methods 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N Cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims 3
- 230000001131 transforming Effects 0.000 claims 3
- 210000001072 Colon Anatomy 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 230000002378 acidificating Effects 0.000 claims 2
- 238000005660 chlorination reaction Methods 0.000 claims 2
- 150000001804 chlorine Chemical class 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 229920001577 copolymer Chemical class 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 238000009434 installation Methods 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 235000010755 mineral Nutrition 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001294 propane Substances 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 2
- 235000011152 sodium sulphate Nutrition 0.000 claims 2
- GBBVHDGKDQAEOT-UHFFFAOYSA-N 1,7-dioxaspiro[5.5]undecane Chemical class O1CCCCC11OCCCC1 GBBVHDGKDQAEOT-UHFFFAOYSA-N 0.000 claims 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims 1
- 101710037290 A674R Proteins 0.000 claims 1
- 101700010952 BAG4 Proteins 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- PUPFATUGTIQBQA-UZQPLGKSSA-N Fluorophen Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@H]2[C@@H]1C)CN2CCC1=CC=C(F)C=C1 PUPFATUGTIQBQA-UZQPLGKSSA-N 0.000 claims 1
- 241001520820 Joinvillea ascendens Species 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- 102100011754 LMNA Human genes 0.000 claims 1
- 101700066012 LMNA Proteins 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- 235000010896 Sesbania bispinosa Nutrition 0.000 claims 1
- 240000003238 Sesbania grandiflora Species 0.000 claims 1
- 235000015392 Sesbania grandiflora Nutrition 0.000 claims 1
- MNWBNISUBARLIT-UHFFFAOYSA-N Sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims 1
- 101700026084 THY1 Proteins 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000001476 alcoholic Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000001430 anti-depressive Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000003001 depressive Effects 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000006263 metalation reaction Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- NGHTXZCKLWZPGK-UHFFFAOYSA-N nefiracetam Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1C(=O)CCC1 NGHTXZCKLWZPGK-UHFFFAOYSA-N 0.000 claims 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical compound [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE631558A true BE631558A (da) |
Family
ID=199983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE631558D BE631558A (da) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE631558A (da) |
-
0
- BE BE631558D patent/BE631558A/fr unknown
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