PL82747B1 - - Google Patents
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- PL82747B1 PL82747B1 PL15524367A PL15524367A PL82747B1 PL 82747 B1 PL82747 B1 PL 82747B1 PL 15524367 A PL15524367 A PL 15524367A PL 15524367 A PL15524367 A PL 15524367A PL 82747 B1 PL82747 B1 PL 82747B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- benzenesulfonyl
- beta
- ethyl
- pattern
- Prior art date
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- -1 chlorocyclohexyl group Chemical group 0.000 claims description 172
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 38
- 235000013877 carbamide Nutrition 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000003003 spiro group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003672 ureas Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 1
- FCHOUYOLBDUXKT-UHFFFAOYSA-N OC(NS(S(C1=CC=CC=C1)(=O)=O)(=O)=O)=O Chemical class OC(NS(S(C1=CC=CC=C1)(=O)=O)(=O)=O)=O FCHOUYOLBDUXKT-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 273
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 238000001953 recrystallisation Methods 0.000 description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 38
- 239000004202 carbamide Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 238000002425 crystallisation Methods 0.000 description 25
- 230000008025 crystallization Effects 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- 239000008280 blood Substances 0.000 description 13
- 210000004369 blood Anatomy 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DCAQNLWAUCQTKO-UHFFFAOYSA-N (3-methoxy-4-methylcyclohexyl)urea Chemical compound COC1CC(NC(N)=O)CCC1C DCAQNLWAUCQTKO-UHFFFAOYSA-N 0.000 description 6
- YKFYIVHNIDHLBO-UHFFFAOYSA-N (4-chlorocyclohexyl)urea Chemical compound NC(=O)NC1CCC(Cl)CC1 YKFYIVHNIDHLBO-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- VNUVSJWIKRAASY-UHFFFAOYSA-N CC(CCC(C1)NC(NS(C2=CC=C(CCNC(C(C=C(C=C3)Cl)=C3OC)=O)C=C2)(=O)=O)=O)C1OC Chemical compound CC(CCC(C1)NC(NS(C2=CC=C(CCNC(C(C=C(C=C3)Cl)=C3OC)=O)C=C2)(=O)=O)=O)C1OC VNUVSJWIKRAASY-UHFFFAOYSA-N 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HANBDOPEUOMZCG-UHFFFAOYSA-N (2-chlorocyclohexyl)urea Chemical compound NC(=O)NC1CCCCC1Cl HANBDOPEUOMZCG-UHFFFAOYSA-N 0.000 description 4
- FZOOOJPISNODNI-UHFFFAOYSA-N 5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(N)=O FZOOOJPISNODNI-UHFFFAOYSA-N 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- ADBNAMBPDJQQAK-UHFFFAOYSA-N ethyl n-[4-[2-[(2-methoxy-5-methylbenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(C)=CC=C1OC ADBNAMBPDJQQAK-UHFFFAOYSA-N 0.000 description 4
- PETZKKYJUCBAIL-UHFFFAOYSA-N ethyl n-[4-[2-[(3-chlorobenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC(Cl)=C1 PETZKKYJUCBAIL-UHFFFAOYSA-N 0.000 description 4
- QQPJYAUUFPBCMK-UHFFFAOYSA-N ethyl n-[4-[2-[(4-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1OC QQPJYAUUFPBCMK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
- 150000001715 carbamic acids Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- SXXBBEZJYUDISU-UHFFFAOYSA-N ethyl n-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC SXXBBEZJYUDISU-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OYAFPGOPLFDDSO-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)Br)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)Br)=C2OC)=O)C=C1)(=O)=O)=O OYAFPGOPLFDDSO-UHFFFAOYSA-N 0.000 description 2
- JBTIKDMEEOWHNF-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OCC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OCC)=O)C=C1)(=O)=O)=O JBTIKDMEEOWHNF-UHFFFAOYSA-N 0.000 description 2
- FBMJVABQSUZJJS-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C2=CC(C)=CC(C)=C2)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C2=CC(C)=CC(C)=C2)=O)C=C1)(=O)=O)=O FBMJVABQSUZJJS-UHFFFAOYSA-N 0.000 description 2
- QIANTASSQORWDD-UHFFFAOYSA-N COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N(C(=O)OCC)C)C=CC=C1 Chemical compound COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N(C(=O)OCC)C)C=CC=C1 QIANTASSQORWDD-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CEPMBCDLZASDSK-UHFFFAOYSA-N N-[2-[4-(carbamoylsulfamoyl)phenyl]ethyl]-5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 CEPMBCDLZASDSK-UHFFFAOYSA-N 0.000 description 2
- AODMIOGGMWOSDI-UHFFFAOYSA-N [3-(benzenesulfonyl)thiophen-2-yl]carbamic acid Chemical class S1C=CC(S(=O)(=O)C=2C=CC=CC=2)=C1NC(=O)O AODMIOGGMWOSDI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical class NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- MJTGQALMWUUPQM-UHFFFAOYSA-N m-Chlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1 MJTGQALMWUUPQM-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 1
- PDJISIIISGZOOQ-UHFFFAOYSA-N 1-chloro-2-isocyanatocyclohexane Chemical compound ClC1CCCCC1N=C=O PDJISIIISGZOOQ-UHFFFAOYSA-N 0.000 description 1
- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical class NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 description 1
- RTZWBJIYBWNJMR-UHFFFAOYSA-N 2-chlorocyclohexan-1-amine Chemical compound NC1CCCCC1Cl RTZWBJIYBWNJMR-UHFFFAOYSA-N 0.000 description 1
- QRBYJPJLVDRGOJ-UHFFFAOYSA-N 2-ethoxy-5-fluorobenzamide Chemical compound CCOC1=CC=C(F)C=C1C(N)=O QRBYJPJLVDRGOJ-UHFFFAOYSA-N 0.000 description 1
- KHYVMZMSUZJVMR-UHFFFAOYSA-N 2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KHYVMZMSUZJVMR-UHFFFAOYSA-N 0.000 description 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 1
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 description 1
- ZMNBXRIYXRBJFL-UHFFFAOYSA-N 3-(4-chlorocyclohexyl)-1,1-diphenylurea Chemical compound C1CC(Cl)CCC1NC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 ZMNBXRIYXRBJFL-UHFFFAOYSA-N 0.000 description 1
- OKFMXCNYDJVSNP-UHFFFAOYSA-N 3-ethoxy-4-methylaniline Chemical compound CCOC1=CC(N)=CC=C1C OKFMXCNYDJVSNP-UHFFFAOYSA-N 0.000 description 1
- YORNKGLZYFTHGX-UHFFFAOYSA-N 3-ethoxy-4-methylcyclohexan-1-amine Chemical compound CCOC1CC(N)CCC1C YORNKGLZYFTHGX-UHFFFAOYSA-N 0.000 description 1
- ONADZNBSLRAJFW-UHFFFAOYSA-N 3-methoxy-4-methylaniline Chemical compound COC1=CC(N)=CC=C1C ONADZNBSLRAJFW-UHFFFAOYSA-N 0.000 description 1
- RVNOGDCEVSPENJ-UHFFFAOYSA-N 3-methylcyclohex-2-ene-1-carboxylic acid Chemical compound CC1=CC(C(O)=O)CCC1 RVNOGDCEVSPENJ-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- KPEWEBCZLHGNCF-UHFFFAOYSA-N 4-chloro-2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KPEWEBCZLHGNCF-UHFFFAOYSA-N 0.000 description 1
- XFVDILBUTKRLKP-UHFFFAOYSA-N 4-chloro-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 XFVDILBUTKRLKP-UHFFFAOYSA-N 0.000 description 1
- SXBXZRWVGWJIEF-UHFFFAOYSA-N 4-chlorocyclohexan-1-amine Chemical compound NC1CCC(Cl)CC1 SXBXZRWVGWJIEF-UHFFFAOYSA-N 0.000 description 1
- LNHHWGZGMYZZRN-UHFFFAOYSA-N 4-isocyanato-2-methoxy-1-methylcyclohexane Chemical compound COC1CC(N=C=O)CCC1C LNHHWGZGMYZZRN-UHFFFAOYSA-N 0.000 description 1
- VWRKGVNZHGRWSV-UHFFFAOYSA-N 5-bromo-2-methoxybenzamide Chemical compound COC1=CC=C(Br)C=C1C(N)=O VWRKGVNZHGRWSV-UHFFFAOYSA-N 0.000 description 1
- KVWWTCSJLGHLRM-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KVWWTCSJLGHLRM-UHFFFAOYSA-N 0.000 description 1
- JCSRHLKQSXRALV-UHFFFAOYSA-N 6-methylcyclohex-2-en-1-amine Chemical compound CC1CCC=CC1N JCSRHLKQSXRALV-UHFFFAOYSA-N 0.000 description 1
- DPZMTCROKBXAMK-UHFFFAOYSA-N 6-methylcyclohex-2-ene-1-carboxylic acid Chemical compound CC1CCC=CC1C(O)=O DPZMTCROKBXAMK-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
- PYAVQEXNCGQXGV-UHFFFAOYSA-N CC1CC(CCC1OC)NC(N)=O Chemical compound CC1CC(CCC1OC)NC(N)=O PYAVQEXNCGQXGV-UHFFFAOYSA-N 0.000 description 1
- PEGZLTNLEMBHPB-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)C(C)=O)=C2OCC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)C(C)=O)=C2OCC)=O)C=C1)(=O)=O)=O PEGZLTNLEMBHPB-UHFFFAOYSA-N 0.000 description 1
- JQPKNQYFRGRBDC-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)OC)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)OC)=C2OC)=O)C=C1)(=O)=O)=O JQPKNQYFRGRBDC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- YDTUUSNRQFOIBD-UHFFFAOYSA-N N-[2-(benzenesulfonamido)ethyl]-5-chloro-2-methoxybenzamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NCCNC(C1=C(C=CC(=C1)Cl)OC)=O YDTUUSNRQFOIBD-UHFFFAOYSA-N 0.000 description 1
- WGKLVFGFFXUXCN-UHFFFAOYSA-N N-[2-[4-(carbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide Chemical compound COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)N)C=CC=C1 WGKLVFGFFXUXCN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- SFEPPJJZTGIQSP-UHFFFAOYSA-N acetic acid;3-methoxy-4-methylcyclohexan-1-amine Chemical compound CC(O)=O.COC1CC(N)CCC1C SFEPPJJZTGIQSP-UHFFFAOYSA-N 0.000 description 1
- JKIRHQCKQJICPL-UHFFFAOYSA-N acetic acid;4-chlorocyclohexan-1-amine Chemical compound CC(O)=O.NC1CCC(Cl)CC1 JKIRHQCKQJICPL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008331 benzenesulfonamides Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- RXFVMUGPHAMQBM-UHFFFAOYSA-N carbonochloridic acid;methanediimine Chemical class N=C=N.OC(Cl)=O RXFVMUGPHAMQBM-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004490 chloroalkoxy group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HWWSINUVAOYFHK-UHFFFAOYSA-N ethyl n-[4-(2-benzamidoethyl)phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC=C1 HWWSINUVAOYFHK-UHFFFAOYSA-N 0.000 description 1
- LTJMXRICHRYYET-UHFFFAOYSA-N ethyl n-methyl-n-[4-[2-[[3-(trifluoromethyl)benzoyl]amino]ethyl]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC(C(F)(F)F)=C1 LTJMXRICHRYYET-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002542 isoureas Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- JITICTFBBGXLFC-UHFFFAOYSA-N n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=CC=C1 JITICTFBBGXLFC-UHFFFAOYSA-N 0.000 description 1
- DWPIKHAKUGBRAE-UHFFFAOYSA-N n-[2-[4-[(2-chlorocyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]benzamide Chemical compound ClC1CCCCC1NC(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=CC=C1 DWPIKHAKUGBRAE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15524367A PL82747B1 (enEXAMPLES) | 1967-05-27 | 1967-05-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15524367A PL82747B1 (enEXAMPLES) | 1967-05-27 | 1967-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82747B1 true PL82747B1 (enEXAMPLES) | 1975-10-31 |
Family
ID=19958488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15524367A PL82747B1 (enEXAMPLES) | 1967-05-27 | 1967-05-27 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL82747B1 (enEXAMPLES) |
-
1967
- 1967-05-27 PL PL15524367A patent/PL82747B1/pl unknown
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