DE2150279C2 - Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom - Google Patents
Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem KohlenstoffatomInfo
- Publication number
- DE2150279C2 DE2150279C2 DE2150279A DE2150279A DE2150279C2 DE 2150279 C2 DE2150279 C2 DE 2150279C2 DE 2150279 A DE2150279 A DE 2150279A DE 2150279 A DE2150279 A DE 2150279A DE 2150279 C2 DE2150279 C2 DE 2150279C2
- Authority
- DE
- Germany
- Prior art keywords
- phenylacetic acid
- pyrimidinyl
- sulfamoyl
- blood sugar
- sulfamoylpyrimidines
- 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.)
- Expired
Links
- 210000004369 blood Anatomy 0.000 title description 5
- 239000008280 blood Substances 0.000 title description 5
- 229910052799 carbon Inorganic materials 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 title 1
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 title 1
- -1 5-neopentyl-2-pyrimidinyl Chemical group 0.000 claims description 10
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FQSSPHAFXLRJBR-UHFFFAOYSA-N 2-(4-chlorosulfonylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(S(Cl)(=O)=O)C=C1 FQSSPHAFXLRJBR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QECSATAUPZYUEL-UHFFFAOYSA-N 2-[4-[[5-(2-methylpropyl)pyrimidin-2-yl]sulfamoyl]phenyl]acetyl chloride Chemical compound C(C(C)C)C=1C=NC(=NC1)NS(=O)(=O)C1=CC=C(C=C1)CC(=O)Cl QECSATAUPZYUEL-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ADSHNWROWDRQOX-UHFFFAOYSA-N 5-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CC1=CN=C(N)N=C1 ADSHNWROWDRQOX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 210000001943 adrenal medulla Anatomy 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WCFCPOKVQRVKAQ-UHFFFAOYSA-N propan-2-ol;propan-2-one;hydrate Chemical compound O.CC(C)O.CC(C)=O WCFCPOKVQRVKAQ-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE789712D BE789712R (fr) | 1970-04-28 | Sulfamoylpyrimidines, a atome de carbone asymetrique, leur procede de preparation et leur | |
| DE2150279A DE2150279C2 (de) | 1971-10-05 | 1971-10-05 | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
| NO713870A NO133138C (enExample) | 1971-10-05 | 1971-10-19 | |
| DK515571A DK136034C (da) | 1971-10-05 | 1971-10-22 | Analogifremgangsmade til fremstilling af sulfamoylpyrimidiner |
| SE7113647A SE385213B (sv) | 1971-10-05 | 1971-10-27 | Sett att framstella blodsockersenkande sulfamoylpyrimidiner med asymmetrisk kolatom |
| CH1193572A CH568982A5 (enExample) | 1971-10-05 | 1972-08-11 | |
| US288590A US3878213A (en) | 1971-03-31 | 1972-09-13 | Certain 4-(n-pyrimidin-2-ylsulfamoyl)-phenylacetamides |
| DD165981A DD103442A6 (enExample) | 1971-10-05 | 1972-10-02 | |
| AT846672A AT319952B (de) | 1971-10-05 | 1972-10-03 | Verfahren zur Herstellung neuer Sulfamoylpyrimidine und ihrer Salze |
| AU47356/72A AU483774B2 (en) | 1971-10-05 | 1972-10-04 | Sulphamoyl-pyrimidines containing an asymmetric 1 carbon atom and having a blood sugar lowering activity |
| FR7235168A FR2158207A2 (en) | 1970-04-28 | 1972-10-04 | Sulphamoyl pyrimidines contg asymmetric carbon atoms |
| NL7213535A NL7213535A (enExample) | 1971-10-05 | 1972-10-05 | |
| JP47100227A JPS4844272A (enExample) | 1971-10-05 | 1972-10-05 | |
| ZA727126A ZA727126B (en) | 1971-10-05 | 1972-10-05 | Sulphamoyl-pyrimidines containing an asymmetric carbon atom and having a blood sugar lowering activity |
| CA153,350A CA977755A (en) | 1971-10-05 | 1972-10-05 | Process for producing sulphamoyl-pyrimidines containing an asymmetric carbon atom and having a blood sugar lowering activity |
| GB4604672A GB1403264A (en) | 1971-10-05 | 1972-10-05 | Sulphamoyl-pyrimidines containing an asymmetric carbon atom and having a blood sugar lowering activity |
| IL40514A IL40514A (en) | 1971-10-05 | 1972-10-05 | Sulphamoyl-pyrimidines containing an asymmetric carbon atom and having a blood sugar lowering activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2150279A DE2150279C2 (de) | 1971-10-05 | 1971-10-05 | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2150279A1 DE2150279A1 (de) | 1973-04-12 |
| DE2150279C2 true DE2150279C2 (de) | 1983-08-25 |
Family
ID=5821847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2150279A Expired DE2150279C2 (de) | 1970-04-28 | 1971-10-05 | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS4844272A (enExample) |
| AT (1) | AT319952B (enExample) |
| CA (1) | CA977755A (enExample) |
| CH (1) | CH568982A5 (enExample) |
| DD (1) | DD103442A6 (enExample) |
| DE (1) | DE2150279C2 (enExample) |
| DK (1) | DK136034C (enExample) |
| GB (1) | GB1403264A (enExample) |
| IL (1) | IL40514A (enExample) |
| NL (1) | NL7213535A (enExample) |
| NO (1) | NO133138C (enExample) |
| SE (1) | SE385213B (enExample) |
| ZA (1) | ZA727126B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3119077A1 (de) * | 1981-05-14 | 1982-12-02 | Basf Ag, 6700 Ludwigshafen | Heterocyclische dihalogenacetmide, verfahren zu ihrer herstellung und herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dihalogenacetamine als antagonistische mittel enthalten |
| BRPI0710487A2 (pt) | 2006-04-12 | 2012-06-05 | Merck & Co Inc | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitácel do mesmo e, método para tratar ou controlar a epilepsia e a dor e para o tratamento ou prevenção de um distúrbio do sono em um paciente. |
| KR20100072266A (ko) | 2007-10-24 | 2010-06-30 | 머크 샤프 앤드 돔 코포레이션 | 헤테로사이클 페닐 아미드 t-형 칼슘 채널 길항제 |
| TW201625588A (zh) * | 2014-11-05 | 2016-07-16 | 第一三共股份有限公司 | 環狀胺衍生物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695855C3 (de) * | 1967-12-30 | 1979-07-12 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 4-(5-Isobutyl-2-pyrimidinyl)-sulfonamidophenylessigsäure-(2-methoxy-5chloranilid) und dessen Salze mit physiologisch verträglichen Basen |
| JPS5516143A (en) * | 1978-07-18 | 1980-02-04 | Yoshihisa Horikoshi | Spindle |
-
1971
- 1971-10-05 DE DE2150279A patent/DE2150279C2/de not_active Expired
- 1971-10-19 NO NO713870A patent/NO133138C/no unknown
- 1971-10-22 DK DK515571A patent/DK136034C/da active
- 1971-10-27 SE SE7113647A patent/SE385213B/xx unknown
-
1972
- 1972-08-11 CH CH1193572A patent/CH568982A5/xx not_active IP Right Cessation
- 1972-10-02 DD DD165981A patent/DD103442A6/xx unknown
- 1972-10-03 AT AT846672A patent/AT319952B/de not_active IP Right Cessation
- 1972-10-05 CA CA153,350A patent/CA977755A/en not_active Expired
- 1972-10-05 NL NL7213535A patent/NL7213535A/xx not_active Application Discontinuation
- 1972-10-05 JP JP47100227A patent/JPS4844272A/ja active Pending
- 1972-10-05 GB GB4604672A patent/GB1403264A/en not_active Expired
- 1972-10-05 IL IL40514A patent/IL40514A/en unknown
- 1972-10-05 ZA ZA727126A patent/ZA727126B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA977755A (en) | 1975-11-11 |
| ZA727126B (en) | 1973-06-27 |
| AU4735672A (en) | 1974-04-11 |
| JPS4844272A (enExample) | 1973-06-26 |
| DK136034C (da) | 1978-01-23 |
| AT319952B (de) | 1975-01-27 |
| CH568982A5 (enExample) | 1975-11-14 |
| IL40514A0 (en) | 1972-12-29 |
| IL40514A (en) | 1976-12-31 |
| NO133138C (enExample) | 1976-03-17 |
| SE385213B (sv) | 1976-06-14 |
| DD103442A6 (enExample) | 1974-01-20 |
| DK136034B (da) | 1977-08-01 |
| GB1403264A (en) | 1975-08-28 |
| NL7213535A (enExample) | 1973-04-09 |
| DE2150279A1 (de) | 1973-04-12 |
| NO133138B (enExample) | 1975-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT363096B (de) | Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen | |
| DE2528360A1 (de) | Neue pyrimidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen | |
| CH641159A5 (de) | Verfahren zur herstellung von neuen guanidinderivaten. | |
| EP0028765B1 (de) | Alkylharnstoffderivate zur Behandlung von Erkrankungen des Fettstoffwechsels; Verfahren zu deren Herstellung, deren Verwendung in Arzneimitteln zur Behandlung von Fettstoffwechselstörungen, diese enthaltende Arzneimittel, Verfahren zur Herstellung der Arzneimittel sowie einige Alkylharnstoffverbindungen | |
| DE2012138B2 (de) | N-eckige klammer auf 4-(beta-pyrazin- 2-carboxyamido-aethyl)-benzolsulphonyl eckige klammer zu -n' - cycloalkylharnstoffe und diese enthaltende pharmazeutische praeparate | |
| DE1695677B1 (de) | N-Arylsulfonyl-N'-(3-aza-bicycloalkyl)-harnstoffe,ihre Salze und Verfahren zu ihrer Herstellung | |
| EP0030650A1 (de) | 1-Piperidinsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung | |
| DE2446758C3 (de) | 2-(2-Fluor-6-trifluormethylphenylimino)-imidazolidin, dessen Säureadditionssalze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung der Hypertonie | |
| DE2150279C2 (de) | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom | |
| EP0132811A1 (de) | In 1-Stellung substituierte 4-Hydroxymethyl-pyrrolidinone, Verfahren zu ihrer Herstellung, pharmazeutische Zusammensetzungen und Zwischenprodukte | |
| DE1940566C3 (de) | 1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel | |
| DE2711225C2 (enExample) | ||
| EP1317430B1 (de) | (2-azabicyclo [2.2.1]hept-7-yl)methanol-derivate als nikotinische acetylcholinrezeptor agonisten | |
| CH628887A5 (de) | Verfahren zur herstellung von benzolsulfonylharnstoffen. | |
| DE1543564A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE1518816C3 (de) | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate | |
| EP0313935A2 (de) | Enolether von 6-Chlor-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno(2,3-e)-1,2-thiazin-3-carbonsäureamid-1,1-dioxid, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE2636866A1 (de) | Neue phenothiazinderivate und deren herstellung | |
| CH474490A (de) | Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe | |
| DE2004301A1 (de) | Phenylserinderivate | |
| DE2027950A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE2833073A1 (de) | Thioharnstoffderivate, verfahren zu ihrer herstellung, verwendung derselben und diese enthaltende arzneimittel | |
| DE2423725A1 (de) | 5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester | |
| DE2031360A1 (de) | Neue cyclische Verbindungen und Ver fahren zu ihrer Herstellung | |
| DE1443908C3 (de) | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8126 | Change of the secondary classification |
Free format text: C07D401/12 A61K 31/505 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |