BE560631A - - Google Patents
Info
- Publication number
- BE560631A BE560631A BE560631DA BE560631A BE 560631 A BE560631 A BE 560631A BE 560631D A BE560631D A BE 560631DA BE 560631 A BE560631 A BE 560631A
- Authority
- BE
- Belgium
- Prior art keywords
- urea
- general formula
- alkali
- sep
- reacted
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 54
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 32
- 239000004202 carbamide Substances 0.000 claims description 23
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 20
- 239000011780 sodium chloride Substances 0.000 claims description 19
- -1 alkaline earth metal salts Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 150000003456 sulfonamides Chemical class 0.000 claims description 15
- AQSQFWLMFCKKMG-UHFFFAOYSA-N 1,3-dibutylurea Chemical compound CCCCNC(=O)NCCCC AQSQFWLMFCKKMG-UHFFFAOYSA-N 0.000 claims description 14
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
- 229960001663 sulfanilamide Drugs 0.000 claims description 7
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 6
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 6
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 6
- 229940026752 topical Sulfonamides Drugs 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- HHHDJHHNEURCNV-UHFFFAOYSA-N p-Chlorobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 claims description 4
- YWXUADNLTYADPN-UHFFFAOYSA-N 1-butyl-3-(4-chlorophenyl)sulfonylurea Chemical class CCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 YWXUADNLTYADPN-UHFFFAOYSA-N 0.000 claims description 3
- JLRGJRBPOGGCBT-UHFFFAOYSA-N N-(p-Tolylsulfonyl)-N'-butylcarbamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- AZEPYUPSYWCRBG-UHFFFAOYSA-N p-Chlorobenzene sulfonyl urea Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 AZEPYUPSYWCRBG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 85
- 235000013877 carbamide Nutrition 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 210000004369 Blood Anatomy 0.000 description 11
- 239000008280 blood Substances 0.000 description 11
- 150000003672 ureas Chemical class 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 230000002218 hypoglycaemic Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- VDTNNGKXZGSZIP-UHFFFAOYSA-N Carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 2
- BBQLCKFJEDETJU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-phenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 BBQLCKFJEDETJU-UHFFFAOYSA-N 0.000 description 2
- MGPSBPIAKKOJQX-UHFFFAOYSA-N 1-butyl-3-(4-nitrophenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 MGPSBPIAKKOJQX-UHFFFAOYSA-N 0.000 description 2
- TYRVXLIAZXPCND-UHFFFAOYSA-N 1-ethyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 TYRVXLIAZXPCND-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- AURPMRPZTDOADA-UHFFFAOYSA-N 1,3-bis(3-methylbutyl)urea Chemical compound CC(C)CCNC(=O)NCCC(C)C AURPMRPZTDOADA-UHFFFAOYSA-N 0.000 description 1
- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- CVYAATGPNZIRSG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(OC)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 CVYAATGPNZIRSG-UHFFFAOYSA-N 0.000 description 1
- XASHKSSTHROXRF-UHFFFAOYSA-N 1-butyl-3-sulfanylurea Chemical compound CCCCNC(=O)NS XASHKSSTHROXRF-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 1
- ZIFOWKKZIWXFJO-UHFFFAOYSA-N N-[4-(butylcarbamoylsulfamoyl)phenyl]acetamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 ZIFOWKKZIWXFJO-UHFFFAOYSA-N 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- YIYZHARUXWKUEN-UHFFFAOYSA-N benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 YIYZHARUXWKUEN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LTSHBNVFPQOLEX-UHFFFAOYSA-N butylbenzene Chemical compound CC[CH]CC1=CC=CC=C1 LTSHBNVFPQOLEX-UHFFFAOYSA-N 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DFTXGSKTFDBVQM-UHFFFAOYSA-N ethyl 4-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 DFTXGSKTFDBVQM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE560631A true BE560631A (pt) |
Family
ID=182856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE560631D BE560631A (pt) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE560631A (pt) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121102A (en) * | 1959-01-26 | 1964-02-11 | Merck & Co Inc | Process for preparing sulfonylureas |
| US3248383A (en) * | 1961-12-27 | 1966-04-26 | Hoechst Ag | Benzenesulfonyl-semicarbazides and process for their manufacture |
-
0
- BE BE560631D patent/BE560631A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121102A (en) * | 1959-01-26 | 1964-02-11 | Merck & Co Inc | Process for preparing sulfonylureas |
| US3248383A (en) * | 1961-12-27 | 1966-04-26 | Hoechst Ag | Benzenesulfonyl-semicarbazides and process for their manufacture |
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