SU440828A1 - - Google Patents
Info
- Publication number
- SU440828A1 SU440828A1 SU1443581A SU1443581A SU440828A1 SU 440828 A1 SU440828 A1 SU 440828A1 SU 1443581 A SU1443581 A SU 1443581A SU 1443581 A SU1443581 A SU 1443581A SU 440828 A1 SU440828 A1 SU 440828A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- urea
- benzenesulfonyl
- methanol
- methoxy
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
- -1 chlorocyclohexyl Chemical group 0.000 description 62
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 53
- 239000004202 carbamide Substances 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 150000001714 carbamic acid halides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 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 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LSDFDZGBOGURGN-UHFFFAOYSA-N ethylbenzene sulfamide Chemical compound S(=O)(=O)(N)N.C(C)C1=CC=CC=C1 LSDFDZGBOGURGN-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- HANBDOPEUOMZCG-UHFFFAOYSA-N (2-chlorocyclohexyl)urea Chemical compound NC(=O)NC1CCCCC1Cl HANBDOPEUOMZCG-UHFFFAOYSA-N 0.000 description 1
- DCAQNLWAUCQTKO-UHFFFAOYSA-N (3-methoxy-4-methylcyclohexyl)urea Chemical compound COC1CC(NC(N)=O)CCC1C DCAQNLWAUCQTKO-UHFFFAOYSA-N 0.000 description 1
- VDTXCHSYBRHTLC-UHFFFAOYSA-N 1,1-diethyl-4-isocyanatocyclohexane Chemical compound CCC1(CC)CCC(N=C=O)CC1 VDTXCHSYBRHTLC-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ASWKQZSDUDPQAO-UHFFFAOYSA-N 3-(4,4-dimethylcyclohexyl)-1,1-diphenylurea Chemical compound C1CC(C)(C)CCC1NC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 ASWKQZSDUDPQAO-UHFFFAOYSA-N 0.000 description 1
- NAYGFGSBOKLOAY-UHFFFAOYSA-N 4,4-diethylcyclohexan-1-amine Chemical compound CCC1(CC)CCC(N)CC1 NAYGFGSBOKLOAY-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BRQSYCGZTLWKGT-UHFFFAOYSA-N CCN(NC(=O)C1=C(C=CC(=C1)Cl)OC)S(=O)(=O)C2=CC=CC=C2 Chemical compound CCN(NC(=O)C1=C(C=CC(=C1)Cl)OC)S(=O)(=O)C2=CC=CC=C2 BRQSYCGZTLWKGT-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- 241001139947 Mida Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- HFNMRUPFYFBJEK-UHFFFAOYSA-N [Na].C(C)NS(=O)(=O)C1=CC=CC=C1 Chemical compound [Na].C(C)NS(=O)(=O)C1=CC=CC=C1 HFNMRUPFYFBJEK-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- OKPTYPHVKNNPSG-UHFFFAOYSA-N n-propylbenzenesulfonamide Chemical compound CCCNS(=O)(=O)C1=CC=CC=C1 OKPTYPHVKNNPSG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])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 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966F0049329 DE1252201B (de) | 1966-05-28 | 1966-05-28 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DE1967F0052152 DE1618402B2 (de) | 1966-05-28 | 1967-04-18 | Benzolsulfonylharnstoffe, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU440828A1 true SU440828A1 (enExample) | 1974-08-25 |
| SU440828A3 SU440828A3 (enExample) | 1974-08-25 |
Family
ID=25977218
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1443581A SU440828A3 (enExample) | 1966-05-28 | 1967-05-27 | |
| SU1443576A SU407445A3 (enExample) | 1966-05-28 | 1967-05-27 | |
| SU1443578A SU465783A3 (ru) | 1966-05-28 | 1967-05-27 | Способ получени бензолсульфонилмочевины |
| SU1444380A SU468403A3 (ru) | 1966-05-28 | 1967-05-28 | Способ получени бензолсульфонилмочевины |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1443576A SU407445A3 (enExample) | 1966-05-28 | 1967-05-27 | |
| SU1443578A SU465783A3 (ru) | 1966-05-28 | 1967-05-27 | Способ получени бензолсульфонилмочевины |
| SU1444380A SU468403A3 (ru) | 1966-05-28 | 1967-05-28 | Способ получени бензолсульфонилмочевины |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5133903B1 (enExample) |
| AR (3) | AR192396A1 (enExample) |
| AT (2) | AT326682B (enExample) |
| BE (1) | BE699134A (enExample) |
| CH (7) | CH502320A (enExample) |
| CY (1) | CY567A (enExample) |
| DE (1) | DE1618402B2 (enExample) |
| DK (1) | DK129414B (enExample) |
| ES (2) | ES340953A1 (enExample) |
| FI (1) | FI46155C (enExample) |
| FR (2) | FR1524754A (enExample) |
| GB (1) | GB1182694A (enExample) |
| IL (1) | IL28034A (enExample) |
| IS (1) | IS734B6 (enExample) |
| LU (1) | LU53740A1 (enExample) |
| MC (1) | MC654A1 (enExample) |
| MY (1) | MY7100059A (enExample) |
| NL (2) | NL157592B (enExample) |
| NO (1) | NO122921B (enExample) |
| OA (1) | OA03625A (enExample) |
| SE (1) | SE336331B (enExample) |
| SU (4) | SU440828A3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES398959A1 (es) * | 1971-01-23 | 1975-09-16 | Hoechst Ag | Procedimiento para la preparacion de bencenosulfonilureas. |
| JP7072586B2 (ja) * | 2017-05-24 | 2022-05-20 | ザ ユニバーシティ オブ クィーンズランド | 新規な化合物及び使用 |
-
1967
- 1967-04-18 DE DE1967F0052152 patent/DE1618402B2/de active Granted
- 1967-05-22 DK DK266367AA patent/DK129414B/da unknown
- 1967-05-23 FI FI671459A patent/FI46155C/fi active
- 1967-05-24 ES ES340953A patent/ES340953A1/es not_active Expired
- 1967-05-24 IS IS1648A patent/IS734B6/is unknown
- 1967-05-24 LU LU53740D patent/LU53740A1/xx unknown
- 1967-05-24 IL IL28034A patent/IL28034A/en unknown
- 1967-05-25 CH CH1948869A patent/CH502320A/de not_active IP Right Cessation
- 1967-05-25 CH CH1948669A patent/CH502318A/de not_active IP Right Cessation
- 1967-05-25 CH CH1948469A patent/CH502998A/de not_active IP Right Cessation
- 1967-05-25 CH CH1948569A patent/CH533090A/de not_active IP Right Cessation
- 1967-05-25 CH CH1948769A patent/CH502319A/de not_active IP Right Cessation
- 1967-05-25 CH CH979571A patent/CH533091A/de not_active IP Right Cessation
- 1967-05-25 CH CH739467A patent/CH503709A/de not_active IP Right Cessation
- 1967-05-26 MC MC694A patent/MC654A1/fr unknown
- 1967-05-26 AT AT375674A patent/AT326682B/de active
- 1967-05-26 AT AT493767A patent/AT324349B/de not_active IP Right Cessation
- 1967-05-26 NL NL6707340.A patent/NL157592B/xx unknown
- 1967-05-26 SE SE07405/67A patent/SE336331B/xx unknown
- 1967-05-27 SU SU1443581A patent/SU440828A3/ru active
- 1967-05-27 NO NO168334A patent/NO122921B/no unknown
- 1967-05-27 SU SU1443576A patent/SU407445A3/ru active
- 1967-05-27 OA OA52951A patent/OA03625A/xx unknown
- 1967-05-27 SU SU1443578A patent/SU465783A3/ru active
- 1967-05-28 SU SU1444380A patent/SU468403A3/ru active
- 1967-05-29 BE BE699134D patent/BE699134A/xx unknown
- 1967-05-29 JP JP42034115A patent/JPS5133903B1/ja active Pending
- 1967-05-29 FR FR108207A patent/FR1524754A/fr not_active Expired
- 1967-05-30 GB GB24852/67A patent/GB1182694A/en not_active Expired
- 1967-08-25 FR FR119022A patent/FR6497M/fr not_active Expired
-
1968
- 1968-05-11 ES ES353814A patent/ES353814A1/es not_active Expired
-
1970
- 1970-04-10 AR AR228019A patent/AR192396A1/es active
- 1970-11-26 CY CY56770A patent/CY567A/xx unknown
-
1971
- 1971-12-30 MY MY59/71A patent/MY7100059A/xx unknown
-
1972
- 1972-12-28 AR AR245895A patent/AR193007A1/es active
- 1972-12-31 AR AR245611A patent/AR192829A1/es active
-
1978
- 1978-02-10 NL NL7801563A patent/NL7801563A/xx unknown
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