CH355447A - Verfahren zur Herstellung von oral wirksamen Antidiabetika - Google Patents

Verfahren zur Herstellung von oral wirksamen Antidiabetika

Info

Publication number: CH355447A
Authority: CH; Switzerland
Prior art keywords: amino group; orally active; antidiabetic agents; production; urea
Prior art date: 1955-07-02

Application number

Other languages

German (de)

English (en)

Inventor

Erich Dr Dipl Chem Haack

Adolf Dr Dipl Chem Hagedorn

Original Assignee

Boehringer & Soehne Gmbh

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.)

1955-07-02

Filing date

1956-04-25

Publication date

1961-07-15

1956-04-25 Application filed by Boehringer & Soehne Gmbh filed Critical Boehringer & Soehne Gmbh

1961-07-15 Publication of CH355447A publication Critical patent/CH355447A/de

Links

239000003472 antidiabetic agent Substances 0.000 title claims description 5
238000000034 method Methods 0.000 title claims description 5
229940125708 antidiabetic agent Drugs 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 6
-1 2-n-pentyl Chemical group 0.000 claims description 5
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 5
229940124530 sulfonamide Drugs 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
POKQNAKXFNFNIE-UHFFFAOYSA-N 1,3-bis[(2-acetyl-4-aminophenyl)sulfonyl]urea Chemical compound C(C)(=O)C1=C(S(=O)(=O)NC(=O)NS(=O)(C2=C(C=C(C=C2)N)C(C)=O)=O)C=CC(=C1)N POKQNAKXFNFNIE-UHFFFAOYSA-N 0.000 description 3
FEEUYJOYDQOMRF-UHFFFAOYSA-N 1-(4-aminophenyl)sulfonyl-1-cyclohexylurea Chemical compound C1(CCCCC1)N(C(=O)N)S(=O)(C1=CC=C(C=C1)N)=O FEEUYJOYDQOMRF-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003456 sulfonamides Chemical class 0.000 description 3
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
QUUJRWWVMWVCEB-UHFFFAOYSA-N (4-amino-2-pentylphenyl)sulfonylurea Chemical compound C(CCCC)C1=C(S(=O)(=O)NC(=O)N)C=CC(=C1)N QUUJRWWVMWVCEB-UHFFFAOYSA-N 0.000 description 2
PXIUJMVWEVKYAN-UHFFFAOYSA-N C1(CCCCC1)NC(N(S(=O)(C1=CC=C(C=C1)N)=O)C(C)=O)=O Chemical compound C1(CCCCC1)NC(N(S(=O)(C1=CC=C(C=C1)N)=O)C(C)=O)=O PXIUJMVWEVKYAN-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
102000004877 Insulin Human genes 0.000 description 2
108090001061 Insulin Proteins 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000003178 anti-diabetic effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229940125396 insulin Drugs 0.000 description 2
PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
VWFHEAWDTBYJKM-UHFFFAOYSA-N CC(N(C(NC1CCCC1)=O)S(C(C=C1)=CC=C1N)(=O)=O)=O Chemical compound CC(N(C(NC1CCCC1)=O)S(C(C=C1)=CC=C1N)(=O)=O)=O VWFHEAWDTBYJKM-UHFFFAOYSA-N 0.000 description 1
ZOHWKDNRLFIQDD-UHFFFAOYSA-N CCCCCCC(N(C(N)=O)S(C(C=C1)=CC=C1N)(=O)=O)=O Chemical compound CCCCCCC(N(C(N)=O)S(C(C=C1)=CC=C1N)(=O)=O)=O ZOHWKDNRLFIQDD-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
208000013016 Hypoglycemia Diseases 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
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
YDLYYDBQQFVYMG-UHFFFAOYSA-N NC(N(C1CCCC1)S(C(C=C1)=CC=C1N)(=O)=O)=O Chemical compound NC(N(C1CCCC1)S(C(C=C1)=CC=C1N)(=O)=O)=O YDLYYDBQQFVYMG-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000003946 cyclohexylamines Chemical class 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical class NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229940127017 oral antidiabetic Drugs 0.000 description 1
IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical class CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 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
230000009257 reactivity Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea

Landscapes

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

CH355447D 1955-07-02 1956-04-25 Verfahren zur Herstellung von oral wirksamen Antidiabetika CH355447A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE355447X		1904-06-24

Publications (1)

Publication Number	Publication Date
CH355447A true CH355447A (de)	1961-07-15

Family

ID=6289981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH355447D CH355447A (de)	1955-07-02	1956-04-25	Verfahren zur Herstellung von oral wirksamen Antidiabetika

Country Status (2)

Country	Link
CH (1)	CH355447A (fr)
FR (1)	FR355447A (fr)

1905
- 1905-06-22 FR FR355447D patent/FR355447A/fr not_active Expired
1956
- 1956-04-25 CH CH355447D patent/CH355447A/de unknown

Also Published As

Publication number	Publication date
FR355447A (fr)	1905-10-31

Publication	Publication Date	Title
CH411849A (de)	1966-04-30	Verfahren zur Herstellung von Hydrindensulfonylharnstoffen
CH355447A (de)	1961-07-15	Verfahren zur Herstellung von oral wirksamen Antidiabetika
CH338185A (de)	1959-05-15	Verfahren zur Herstellung eines oral wirksamen Antidiabetikums
DE1003716B (de)	1957-03-07	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
DE2050979A1 (de)	1971-04-29	Thiadiazole und ihre Verwendung als landwirtschaftliche Pestizide
DE1011413B (de)	1957-07-04	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT200583B (de)	1958-11-10	Verfahren zur Herstellung von neuen Sulfonylurethanen
DE963514C (de)	1957-05-09	Verfahren zur Herstellung schwerloeslicher kristallisierter Streptomycin- und Dihydrostreptomycinsalze
CH338186A (de)	1959-05-15	Verfahren zur Herstellung eines oralen Antidiabetikums
CH509992A (de)	1971-07-15	Verfahren zur Herstellung von Sulfonamiden
AT216008B (de)	1961-07-10	Verfahren zur Herstellung neuen Sulfonylharnstoffe
DE3812208A1 (de)	1989-10-26	Verfahren zur herstellung von 4-guanidinomethyl-cyclohexancarbonsaeure
CH353348A (de)	1961-04-15	Verfahren zur Herstellung von oral wirksamen Antidiabetika
DE1012598B (de)	1957-07-25	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT220626B (de)	1962-04-10	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
AT319960B (de)	1975-01-27	Verfahren zur Herstellung von neuen Pyridazinverbindungen
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT233584B (de)	1964-05-11	Verfahren zur Herstellung von neuen Hydrindensulfonylharnstoffen
DE947165C (de)	1956-08-09	Verfahren zur Herstellung von in 3-Stellung substituierten 4-Oxycumarinen
DE1219489B (de)	1966-06-23	Verfahren zur Herstellung von substituierten 5-Thioureidouracilen
CH500186A (de)	1970-12-15	Verfahren zur Herstellung von Pyrrolidinverbindungen
DE1036563B (de)	1958-08-14	Fungizide Mittel
CH263801A (de)	1949-09-15	Verfahren zur Herstellung eines Tertiär-alkyl-aminsalzes.
DE1037443B (de)	1958-08-28	Verfahren zur Herstellung von narkotisch wirkenden Carbamaten
CH371108A (de)	1963-08-15	Verfahren zur Herstellung von Sulfonylharnstoffen