CH385865A - Verfahren zur Herstellung von neuen 2-Sulfonamidothia-diazol-Derivaten - Google Patents

Verfahren zur Herstellung von neuen 2-Sulfonamidothia-diazol-Derivaten

Info

Publication number: CH385865A
Authority: CH; Switzerland
Prior art keywords: thiadiazole; radical; formula; amino; pyridine
Prior art date: 1957-12-21

Application number

CH6748758A

Other languages

German (de)

English (en)

Inventor

Rudi Dr Weyer

Walter Dr Aumueller

Gerhard Dr Korger

Josef Dr Scholz

Alfred Dr Baender

Erich Dr Haack

Original Assignee

Hoechst 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.)

1957-12-21

Filing date

1958-12-19

Publication date

1964-12-31

1958-12-19 Application filed by Hoechst Ag filed Critical Hoechst Ag

1964-12-31 Publication of CH385865A publication Critical patent/CH385865A/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 7
-1 tetrahydronaphthalene radical Chemical class 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000012286 potassium permanganate Substances 0.000 claims description 3
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 57
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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239000000126 substance Substances 0.000 description 9
239000002253 acid Substances 0.000 description 7
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239000000706 filtrate Substances 0.000 description 6
229940124530 sulfonamide Drugs 0.000 description 6
239000002244 precipitate Substances 0.000 description 5
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IGBPZWZBEPBBTR-UHFFFAOYSA-N 5-propan-2-yl-1,3,4-thiadiazol-2-amine Chemical compound CC(C)C1=NN=C(N)S1 IGBPZWZBEPBBTR-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 3
OSRUOEPCJQGHMV-UHFFFAOYSA-N 4-methyl-n-(5-pentyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(CCCCC)=NN=C1NS(=O)(=O)C1=CC=C(C)C=C1 OSRUOEPCJQGHMV-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 2
WAHFYBHQGSHRJD-UHFFFAOYSA-N 2-butyl-1,3,4-thiadiazole Chemical compound CCCCC1=NN=CS1 WAHFYBHQGSHRJD-UHFFFAOYSA-N 0.000 description 2
NMVRKOPWCBGSDK-UHFFFAOYSA-N 2-butylbenzenesulfonyl chloride Chemical compound CCCCC1=CC=CC=C1S(Cl)(=O)=O NMVRKOPWCBGSDK-UHFFFAOYSA-N 0.000 description 2
GMEMYBMFSHDTNQ-UHFFFAOYSA-N 3,4-dimethoxy-N-(5-propyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(CCC)=NN=C1NS(=O)(=O)C1=CC=C(OC)C(OC)=C1 GMEMYBMFSHDTNQ-UHFFFAOYSA-N 0.000 description 2
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
DCOUGMGNHGFYQI-UHFFFAOYSA-N 4-methoxy-n-(5-propan-2-yl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NN=C(C(C)C)S1 DCOUGMGNHGFYQI-UHFFFAOYSA-N 0.000 description 2
PCAGBWNSEHFSDS-UHFFFAOYSA-N 4-methyl-n-[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]benzenesulfonamide Chemical compound S1C(CC(C)C)=NN=C1NS(=O)(=O)C1=CC=C(C)C=C1 PCAGBWNSEHFSDS-UHFFFAOYSA-N 0.000 description 2
FNEIMPFRVQQOMV-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride Chemical compound C1CCCC2=CC(S(=O)(=O)Cl)=CC=C21 FNEIMPFRVQQOMV-UHFFFAOYSA-N 0.000 description 2
BLBDGPFJLDEFFL-UHFFFAOYSA-N 5-cyclohexyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCCC1 BLBDGPFJLDEFFL-UHFFFAOYSA-N 0.000 description 2
NLQURINLKRAGIF-UHFFFAOYSA-N 5-propyl-1,3,4-thiadiazol-2-amine Chemical compound CCCC1=NN=C(N)S1 NLQURINLKRAGIF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
WJRGTDUJYSATSA-UHFFFAOYSA-N CC(C)CC1=NN=C(NS(C2=C(C)C=CC=C2Cl)(=O)=O)S1 Chemical compound CC(C)CC1=NN=C(NS(C2=C(C)C=CC=C2Cl)(=O)=O)S1 WJRGTDUJYSATSA-UHFFFAOYSA-N 0.000 description 2
UGOIYMNLERVDCS-UHFFFAOYSA-N CC(C)CC1=NN=C(NS(C2=CC=C(C(C)(C)C)C=C2)(=O)=O)S1 Chemical compound CC(C)CC1=NN=C(NS(C2=CC=C(C(C)(C)C)C=C2)(=O)=O)S1 UGOIYMNLERVDCS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
230000003385 bacteriostatic effect Effects 0.000 description 2
230000000973 chemotherapeutic effect Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
238000000227 grinding Methods 0.000 description 2
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 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
RTXZQECDUNSBPT-UHFFFAOYSA-N n-(5-ethyl-1,3,4-thiadiazol-2-yl)-4-methylbenzenesulfonamide Chemical compound S1C(CC)=NN=C1NS(=O)(=O)C1=CC=C(C)C=C1 RTXZQECDUNSBPT-UHFFFAOYSA-N 0.000 description 2
ZMZGBETXVNWFHN-UHFFFAOYSA-N n-[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]-1-phenylmethanesulfonamide Chemical compound S1C(CC(C)C)=NN=C1NS(=O)(=O)CC1=CC=CC=C1 ZMZGBETXVNWFHN-UHFFFAOYSA-N 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
QONVWLTTWDJSHM-UHFFFAOYSA-N 1-phenylethanesulfonyl chloride Chemical compound ClS(=O)(=O)C(C)C1=CC=CC=C1 QONVWLTTWDJSHM-UHFFFAOYSA-N 0.000 description 1
CLAYHWKWFNAKCG-UHFFFAOYSA-N 2-(2-methylpropyl)-1,3,4-thiadiazole Chemical compound CC(C)CC1=NN=CS1 CLAYHWKWFNAKCG-UHFFFAOYSA-N 0.000 description 1
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MDJWJISHGWJZAC-UHFFFAOYSA-N 2-cyclohexyl-1,3,4-thiadiazole Chemical compound C1CCCCC1C1=NN=CS1 MDJWJISHGWJZAC-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
RSJSYCZYQNJQPY-UHFFFAOYSA-N 3,4-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1OC RSJSYCZYQNJQPY-UHFFFAOYSA-N 0.000 description 1
DNMQPRPJIWTNAX-UHFFFAOYSA-N 3,4-dimethylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1C DNMQPRPJIWTNAX-UHFFFAOYSA-N 0.000 description 1
UFESGJFEJHJCON-UHFFFAOYSA-N 3-chloro-2-methoxybenzenesulfonyl chloride Chemical compound COC1=C(Cl)C=CC=C1S(Cl)(=O)=O UFESGJFEJHJCON-UHFFFAOYSA-N 0.000 description 1
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JHJKSEKUZNJKGO-UHFFFAOYSA-N 3-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC(S(Cl)(=O)=O)=C1 JHJKSEKUZNJKGO-UHFFFAOYSA-N 0.000 description 1
KFPMLWUKHQMEBU-UHFFFAOYSA-N 3-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(S(Cl)(=O)=O)=C1 KFPMLWUKHQMEBU-UHFFFAOYSA-N 0.000 description 1
SVYBEBLNQGDRHF-UHFFFAOYSA-N 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(CC)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 SVYBEBLNQGDRHF-UHFFFAOYSA-N 0.000 description 1
UPOKWSNHWXFXDF-UHFFFAOYSA-N 4-amino-N-(thiadiazol-4-yl)benzenesulfonamide Chemical class C1=CC(N)=CC=C1S(=O)(=O)NC1=CSN=N1 UPOKWSNHWXFXDF-UHFFFAOYSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
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HGKWMUBXVMFXNC-UHFFFAOYSA-N 4-butoxybenzenesulfonyl chloride Chemical compound CCCCOC1=CC=C(S(Cl)(=O)=O)C=C1 HGKWMUBXVMFXNC-UHFFFAOYSA-N 0.000 description 1
XQHVRNDTDHAEPK-UHFFFAOYSA-N 4-chloro-n-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NN=C(C2CCCCC2)S1 XQHVRNDTDHAEPK-UHFFFAOYSA-N 0.000 description 1
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XIWSSFMVSKKXRJ-UHFFFAOYSA-N 4-ethoxybenzenesulfonyl chloride Chemical compound CCOC1=CC=C(S(Cl)(=O)=O)C=C1 XIWSSFMVSKKXRJ-UHFFFAOYSA-N 0.000 description 1
LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 1
CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 1
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HCROFIOWOLVVEA-UHFFFAOYSA-N 5-(2-methylpropyl)-3H-thiadiazol-2-amine Chemical compound NN1SC(=CN1)CC(C)C HCROFIOWOLVVEA-UHFFFAOYSA-N 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
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RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
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 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
238000000354 decomposition reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000004519 grease Substances 0.000 description 1
230000026781 habituation Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000968 intestinal effect Effects 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
239000008101 lactose Substances 0.000 description 1
238000012153 long-term therapy Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PEEIQUTYAXMFHG-UHFFFAOYSA-N n-(5-propan-2-yl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(C(C)C)=NN=C1NS(=O)(=O)C1=CC=CC=C1 PEEIQUTYAXMFHG-UHFFFAOYSA-N 0.000 description 1
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000926 not very toxic Toxicity 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001685 thyroid gland Anatomy 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
238000011282 treatment Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CH6748758A 1957-12-21 1958-12-19 Verfahren zur Herstellung von neuen 2-Sulfonamidothia-diazol-Derivaten CH385865A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0024671		1957-12-21

Publications (1)

Publication Number	Publication Date
CH385865A true CH385865A (de)	1964-12-31

Family

ID=7091318

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH6748758A CH385865A (de)	1957-12-21	1958-12-19	Verfahren zur Herstellung von neuen 2-Sulfonamidothia-diazol-Derivaten
CH157364A CH385867A (de)	1957-12-21	1958-12-19	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten
CH157464A CH385868A (de)	1957-12-21	1958-12-19	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH157364A CH385867A (de)	1957-12-21	1958-12-19	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten
CH157464A CH385868A (de)	1957-12-21	1958-12-19	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten

Country Status (2)

Country	Link
BE (1)	BE574133A (fr)
CH (3)	CH385865A (fr)

1958
- 1958-12-19 CH CH6748758A patent/CH385865A/de unknown
- 1958-12-19 CH CH157364A patent/CH385867A/de unknown
- 1958-12-19 CH CH157464A patent/CH385868A/de unknown
- 1958-12-22 BE BE574133A patent/BE574133A/fr unknown

Also Published As

Publication number	Publication date
BE574133A (fr)	1959-06-22
CH385867A (de)	1964-12-31
CH385868A (de)	1964-12-31

Publication	Publication Date	Title
DE2602643C2 (de)	1984-12-20	1,2-Benzisothiazolinone-3, Verfahren zu ihrer Herstellung sowie Arzneimittel
CH385865A (de)	1964-12-31	Verfahren zur Herstellung von neuen 2-Sulfonamidothia-diazol-Derivaten
DE2143744A1 (de)	1973-03-08	3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung
AT212312B (de)	1960-12-12	Verfahren zur Herstellung von neuen 2-Sulfonamidothiadiazol-Derivaten
CH392497A (de)	1965-05-31	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
CH370766A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
CH441274A (de)	1967-08-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT226729B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1668199B2 (de)	1976-06-24	Benzolsulfonyl-3-(2-hydroxycyclohexyl)harnstoffe
AT238215B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1011413B (de)	1957-07-04	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT200583B (de)	1958-11-10	Verfahren zur Herstellung von neuen Sulfonylurethanen
CH353348A (de)	1961-04-15	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT211310B (de)	1960-10-10	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten
CH363652A (de)	1962-08-15	Verfahren zur Herstellung von Sulfonylharnstoffen
CH465597A (de)	1968-11-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
DE1199765B (de)	1965-09-02	Verfahren zur Herstellung von Benzolsulfonyl-harnstoffderivaten
CH380097A (de)	1964-07-31	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen
CH410985A (de)	1966-04-15	Verfahren zur Herstellung von Additionsverbindungen von Sulfonsäurehydraziden mit organischen Sulfonsäuren
CH406184A (de)	1966-01-31	Verfahren zur Herstellung von Mercaptonen und Verwendung derselben
DE1076664B (de)	1960-03-03	Verfahren zur Herstellung von neuen N-Benzolsulfonyl-N'-benzyl-harnstoffen
DE1545902A1 (de)	1969-11-27	Verfahren zur Herstellung von neuen Imidazolderivaten
CH380717A (de)	1964-08-15	Verfahren zur Herstellung von neuen Sulfonylharnstoffen