DE1770731A1 - Neue blutzuckersenkende Sulfonamide - Google Patents
Neue blutzuckersenkende SulfonamideInfo
- Publication number
- DE1770731A1 DE1770731A1 DE19681770731 DE1770731A DE1770731A1 DE 1770731 A1 DE1770731 A1 DE 1770731A1 DE 19681770731 DE19681770731 DE 19681770731 DE 1770731 A DE1770731 A DE 1770731A DE 1770731 A1 DE1770731 A1 DE 1770731A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- carbonamido
- meaning given
- given above
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 229940124530 sulfonamide Drugs 0.000 title description 7
- 150000003456 sulfonamides Chemical class 0.000 title description 7
- 239000008280 blood Substances 0.000 title description 2
- 210000004369 blood Anatomy 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 ethylbenzenesulfonamido Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical class O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940118019 malondialdehyde Drugs 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 101150033922 ABCA2 gene Proteins 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- OIEZCWFCXVSIGQ-UHFFFAOYSA-N 1,1-diethoxy-4-methylpentane Chemical compound CCOC(OCC)CCC(C)C OIEZCWFCXVSIGQ-UHFFFAOYSA-N 0.000 description 1
- ZINCSSQSZVBPDS-UHFFFAOYSA-N 2-chloro-5-propan-2-yloxypyrimidine Chemical compound CC(C)OC1=CN=C(Cl)N=C1 ZINCSSQSZVBPDS-UHFFFAOYSA-N 0.000 description 1
- YAKIJEZSDKOGGQ-UHFFFAOYSA-N 5-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CC1=CN=C(N)N=C1 YAKIJEZSDKOGGQ-UHFFFAOYSA-N 0.000 description 1
- ZTRBLDGFVYAFEK-UHFFFAOYSA-N 5-(2-methylpropyl)pyrimidine Chemical compound CC(C)CC1=CN=CN=C1 ZTRBLDGFVYAFEK-UHFFFAOYSA-N 0.000 description 1
- SKXUYGMCEKFULT-UHFFFAOYSA-N 5-butoxypyrimidine Chemical compound C(CCC)OC=1C=NC=NC1 SKXUYGMCEKFULT-UHFFFAOYSA-N 0.000 description 1
- IYXYRUPBYNCTNU-UHFFFAOYSA-N 5-propan-2-yloxypyrimidine Chemical compound CC(C)OC1=CN=CN=C1 IYXYRUPBYNCTNU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770731 DE1770731A1 (de) | 1968-06-27 | 1968-06-27 | Neue blutzuckersenkende Sulfonamide |
| BR208777/69A BR6908777D0 (pt) | 1968-06-27 | 1969-05-14 | Processo para a preparacao de novas sulfonamidas |
| DK300869AA DK123602B (da) | 1968-06-27 | 1969-06-03 | Analogifremgangsmåde til fremstilling af sulfonamider. |
| CH1669171A CH518970A (de) | 1968-06-27 | 1969-06-05 | Verfahren zur Herstellung neuer Sulfonamide |
| CH1669271A CH518971A (de) | 1968-06-27 | 1969-06-05 | Verfahren zur Herstellung neuer Sulfonamide |
| CH860269A CH518968A (de) | 1968-06-27 | 1969-06-05 | Verfahren zur Herstellung von neuen Sulfonamiden |
| ES368100A ES368100A1 (es) | 1968-06-27 | 1969-06-06 | Procedimiento para la preparacion de nuevas sulfonamidas que reducen el azucar en la sangre. |
| IL32396A IL32396A (en) | 1968-06-27 | 1969-06-13 | Hypoglycemic benzene sulphonamido-2-pyrimidine derivatives |
| GB30406/69A GB1268835A (en) | 1968-06-27 | 1969-06-16 | New sulphonamides having a blood sugar lowering action |
| AT788870A AT291256B (de) | 1968-06-27 | 1969-06-17 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen und ihren Salzen |
| AT788770A AT291255B (de) | 1968-06-27 | 1969-06-17 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen und ihren Salzen |
| AT573169A AT289109B (de) | 1968-06-27 | 1969-06-17 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen und ihren Salzen |
| SE08952/69A SE357365B (enrdf_load_stackoverflow) | 1968-06-27 | 1969-06-24 | |
| IE873/69A IE33175B1 (en) | 1968-06-27 | 1969-06-25 | New sulphonamides having a blood sugar lowering action |
| NO2659/69A NO124374B (enrdf_load_stackoverflow) | 1968-06-27 | 1969-06-26 | |
| FR696921467A FR2014300B1 (enrdf_load_stackoverflow) | 1968-06-27 | 1969-06-26 | |
| NL6909960A NL6909960A (enrdf_load_stackoverflow) | 1968-06-27 | 1969-06-27 | |
| BE735287D BE735287A (enrdf_load_stackoverflow) | 1968-06-27 | 1969-06-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770731 DE1770731A1 (de) | 1968-06-27 | 1968-06-27 | Neue blutzuckersenkende Sulfonamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770731A1 true DE1770731A1 (de) | 1971-11-25 |
Family
ID=5700618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770731 Pending DE1770731A1 (de) | 1968-06-27 | 1968-06-27 | Neue blutzuckersenkende Sulfonamide |
Country Status (14)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2048906A1 (de) * | 1970-10-06 | 1972-04-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
| EP1521577A1 (en) * | 2002-06-13 | 2005-04-13 | QLT, Inc. | Methods of using isothiazole derivatives to treat cancer or inflammation |
-
1968
- 1968-06-27 DE DE19681770731 patent/DE1770731A1/de active Pending
-
1969
- 1969-05-14 BR BR208777/69A patent/BR6908777D0/pt unknown
- 1969-06-03 DK DK300869AA patent/DK123602B/da unknown
- 1969-06-05 CH CH860269A patent/CH518968A/de not_active IP Right Cessation
- 1969-06-06 ES ES368100A patent/ES368100A1/es not_active Expired
- 1969-06-13 IL IL32396A patent/IL32396A/xx unknown
- 1969-06-16 GB GB30406/69A patent/GB1268835A/en not_active Expired
- 1969-06-17 AT AT788870A patent/AT291256B/de not_active IP Right Cessation
- 1969-06-17 AT AT788770A patent/AT291255B/de not_active IP Right Cessation
- 1969-06-17 AT AT573169A patent/AT289109B/de not_active IP Right Cessation
- 1969-06-24 SE SE08952/69A patent/SE357365B/xx unknown
- 1969-06-25 IE IE873/69A patent/IE33175B1/xx unknown
- 1969-06-26 FR FR696921467A patent/FR2014300B1/fr not_active Expired
- 1969-06-26 NO NO2659/69A patent/NO124374B/no unknown
- 1969-06-27 NL NL6909960A patent/NL6909960A/xx unknown
- 1969-06-27 BE BE735287D patent/BE735287A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1268835A (en) | 1972-03-29 |
| FR2014300B1 (enrdf_load_stackoverflow) | 1973-01-12 |
| DK123602B (da) | 1972-07-10 |
| AT291256B (de) | 1971-07-12 |
| NL6909960A (enrdf_load_stackoverflow) | 1969-12-30 |
| NO124374B (enrdf_load_stackoverflow) | 1972-04-10 |
| IL32396A (en) | 1972-06-28 |
| IL32396A0 (en) | 1969-08-27 |
| AT291255B (de) | 1971-07-12 |
| FR2014300A1 (enrdf_load_stackoverflow) | 1970-04-17 |
| ES368100A1 (es) | 1971-05-01 |
| AT289109B (de) | 1971-04-13 |
| BE735287A (enrdf_load_stackoverflow) | 1969-12-29 |
| IE33175B1 (en) | 1974-04-03 |
| CH518968A (de) | 1972-02-15 |
| IE33175L (en) | 1969-12-27 |
| SE357365B (enrdf_load_stackoverflow) | 1973-06-25 |
| BR6908777D0 (pt) | 1973-01-23 |
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