CH505830A - Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids - Google Patents

Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids

Info

Publication number: CH505830A
Authority: CH; Switzerland
Prior art keywords: acid; methyl; general formula; group; radical
Prior art date: 1968-03-14

Application number

CH388568A

Other languages

German (de)

English (en)

Inventor

Henri Dr Dietrich

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-03-14

Filing date

1968-03-14

Publication date

1971-04-15

1968-03-14 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1968-03-14 Priority to CH388568A priority Critical patent/CH505830A/de

1969-03-12 Priority to NL6903832A priority patent/NL6903832A/xx

1969-03-13 Priority to IL31799A priority patent/IL31799A/en

1969-03-13 Priority to BE729835D priority patent/BE729835A/xx

1969-03-13 Priority to IE335/69A priority patent/IE32674B1/xx

1969-03-13 Priority to ES364712A priority patent/ES364712A1/es

1969-03-13 Priority to ES364713A priority patent/ES364713A1/es

1969-03-13 Priority to CA045,554A priority patent/CA971958A/en

1969-03-13 Priority to PL13232569A priority patent/PL69824B1/pl

1969-03-13 Priority to DE19691912848 priority patent/DE1912848A1/de

1969-03-13 Priority to AT1159069A priority patent/AT288377B/de

1969-03-14 Priority to GB03508/69A priority patent/GB1261572A/en

1971-02-20 Priority to JP46007922A priority patent/JPS49184B1/ja

1971-04-15 Publication of CH505830A publication Critical patent/CH505830A/de

Links

FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims description 4
230000002218 hypoglycaemic effect Effects 0.000 title abstract description 4
229940124530 sulfonamide Drugs 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
230000009467 reduction Effects 0.000 claims description 6
238000006722 reduction reaction Methods 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
238000006894 reductive elimination reaction Methods 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 3
150000005690 diesters Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
230000002829 reductive effect Effects 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 4
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
-1 1-sulfanilyl-2-imino-3-butyl- Chemical group 0.000 description 53
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960001413 acetanilide Drugs 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NPIBJJMMZTYXPQ-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=N)NCCCC Chemical compound C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=N)NCCCC NPIBJJMMZTYXPQ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KIAFJFXFFGIKKC-UHFFFAOYSA-N 4-(2-imino-3-pentylimidazolidin-1-yl)sulfonylaniline Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)N1C(N(CC1)CCCCC)=N KIAFJFXFFGIKKC-UHFFFAOYSA-N 0.000 description 1
QITIFNUPQIRBPD-UHFFFAOYSA-N 4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 QITIFNUPQIRBPD-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
TXOZOSNONGVLBY-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=N)NC1CCCCC1 Chemical compound C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(=N)NC1CCCCC1 TXOZOSNONGVLBY-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
241001465754 Metazoa Species 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
RBFQHDCKMMMAHK-UHFFFAOYSA-N N-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]acetamide Chemical compound N=C1N(CCN1C1CCCCC1)S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 RBFQHDCKMMMAHK-UHFFFAOYSA-N 0.000 description 1
241000798077 Poelagus marjorita Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
RPRIFTWWESFXAM-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)N1C(N(CC1)CCCC)=N Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)N1C(N(CC1)CCCC)=N RPRIFTWWESFXAM-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH388568A 1968-03-14 1968-03-14 Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids CH505830A (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH388568A CH505830A (de)	1968-03-14	1968-03-14	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
NL6903832A NL6903832A (pl)	1968-03-14	1969-03-12
IL31799A IL31799A (en)	1968-03-14	1969-03-13	Processes for the preparation of 1-sulphanilyl-2-imino-imidazolidine derivatives
BE729835D BE729835A (pl)	1968-03-14	1969-03-13
IE335/69A IE32674B1 (en)	1968-03-14	1969-03-13	Sulfanilamide derivatives their preparation and use
ES364712A ES364712A1 (es)	1968-03-14	1969-03-13	Procedimiento para la preparacion de nuevos derivados de sulfanilamida.
ES364713A ES364713A1 (es)	1968-03-14	1969-03-13	Procedimiento para la preparacion de nuevos derivados de sulfanilamida.
CA045,554A CA971958A (en)	1968-03-14	1969-03-13	Process for the production of new sulphanilamide derivatives
PL13232569A PL69824B1 (pl)	1968-03-14	1969-03-13
DE19691912848 DE1912848A1 (de)	1968-03-14	1969-03-13	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
AT1159069A AT288377B (de)	1968-03-14	1969-03-13	Verfahren zur Herstellung von neuen Imidazolidinderivaten und ihren Salzen
GB03508/69A GB1261572A (en)	1968-03-14	1969-03-14	Sulfanilamide derivatives their preparation and use
JP46007922A JPS49184B1 (pl)	1968-03-14	1971-02-20

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH388568A CH505830A (de)	1968-03-14	1968-03-14	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids

Publications (1)

Publication Number	Publication Date
CH505830A true CH505830A (de)	1971-04-15

Family

ID=4265590

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH388568A CH505830A (de)	1968-03-14	1968-03-14	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids

Country Status (4)

Country	Link
AT (1)	AT288377B (pl)
CH (1)	CH505830A (pl)
ES (2)	ES364713A1 (pl)
PL (1)	PL69824B1 (pl)

1968
- 1968-03-14 CH CH388568A patent/CH505830A/de not_active IP Right Cessation
1969
- 1969-03-13 PL PL13232569A patent/PL69824B1/pl unknown
- 1969-03-13 AT AT1159069A patent/AT288377B/de not_active IP Right Cessation
- 1969-03-13 ES ES364713A patent/ES364713A1/es not_active Expired
- 1969-03-13 ES ES364712A patent/ES364712A1/es not_active Expired

Also Published As

Publication number	Publication date
AT288377B (de)	1971-03-10
PL69824B1 (pl)	1973-10-31
ES364712A1 (es)	1970-12-16
ES364713A1 (es)	1970-12-16

Legal Events

Date	Code	Title	Description
1976-10-15	PL	Patent ceased

Publication	Publication Date	Title
EP0287907B1 (de)	1992-08-19	Pyrazolo[3,4-d]pyrimidine, Verfahren zu ihrer Herstellung und Verwendung als Arzneimittel
DE2062001C2 (de)	1986-10-16	1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches Präparat
DE1795193C2 (de)	1984-08-23	Isochinolinderivate und Verfahren zur Herstellung von N-Methylmorphinanen
DE2141616B2 (de)	1974-08-22	Oxazolo- und Oxazine eckige Klammer auf 3,2-c eckige Klammer zu chinazolinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2710246A1 (de)	1977-09-22	Delta hoch 8 -ergolen- beziehungsweise ergolinderivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben
DE3642497A1 (de)	1988-06-23	Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte
DE1802297C3 (de)	1974-10-17	Isopropylaminderivate und Verfahren zu ihrer Herstellung
US2980693A (en)	1961-04-18	Methods for producing same
DE1620342C3 (pl)	1974-05-16
DE907530C (de)	1954-03-25	Verfahren zur Herstellung von analgetisch wirkenden Derivaten des 1-Oxyphenyl-3-aminobutans
CH504444A (de)	1971-03-15	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
CH535236A (de)	1973-03-31	Verfahren zur Herstellung neuer reaktionsträger Lysergsäurederivate
CH500988A (de)	1970-12-31	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
DE3146785A1 (de)	1982-07-01	"verfahren zur herstellung von 16(alpha)-hydroxy-17(alpha)-aminopregnanderivaten und ihre verwendung"
CH507953A (de)	1971-05-31	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
CH455777A (de)	1968-05-15	Verfahren zur Herstellung von neuen Indolderivaten
DE2331044A1 (de)	1974-01-10	Diphenylmethan-derivate und verfahren zu deren herstellung
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
DE1445123C (de)	1973-07-19	7 substituierte 10 (beta Amino athyl) 10,11 dihydrodibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepinon (11) derivate
AT214427B (de)	1961-04-10	Verfahren zur Herstellung neuer basischer Phenoläther
CH535235A (de)	1973-03-31	Verfahren zur Herstellung neuer reaktionsträger Lysergsäurederivate
AT219611B (de)	1962-02-12	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen und deren Salzen
DE2434015A1 (de)	1975-04-03	1-phenyl-6-azabicyclo eckige klammer auf 3,2,1 eckige klammer zu octanderivate, verfahren zu deren herstellung und dieselben enthaltendes mittel
DE2338409A1 (de)	1975-02-13	Neues verfahren zur herstellung von 2-acylamino-benzylaminen
CH602766A5 (en)	1978-07-31	10-Alpha-methoxy-di:hydro-beta-ergosine derivs.