DE2111557C3 - 1 -(3-SuIfamoyl-4-chlor-benzamido) -3-(2-furyl)-pyrrolidin und ein Verfahren zu dessen Herstellung - Google Patents
1 -(3-SuIfamoyl-4-chlor-benzamido) -3-(2-furyl)-pyrrolidin und ein Verfahren zu dessen HerstellungInfo
- Publication number
- DE2111557C3 DE2111557C3 DE2111557A DE2111557A DE2111557C3 DE 2111557 C3 DE2111557 C3 DE 2111557C3 DE 2111557 A DE2111557 A DE 2111557A DE 2111557 A DE2111557 A DE 2111557A DE 2111557 C3 DE2111557 C3 DE 2111557C3
- Authority
- DE
- Germany
- Prior art keywords
- hours
- pyrrolidine
- furyl
- chloro
- animals
- 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
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- ATNKMDQAKYYZMP-UHFFFAOYSA-N 4-chloro-n-[3-(furan-2-yl)pyrrolidin-1-yl]-3-sulfamoylbenzamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NN2CC(CC2)C=2OC=CC=2)=C1 ATNKMDQAKYYZMP-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
- 230000029142 excretion Effects 0.000 description 9
- 210000002700 urine Anatomy 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 239000000126 substance Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011835 investigation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000003792 electrolyte 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
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- -1 3-sulfamoyl-4-chloro-benzamido Chemical group 0.000 description 1
- SCYSJFKWFQZRJW-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Cl SCYSJFKWFQZRJW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB01430/70A GB1280393A (en) | 1970-03-10 | 1970-03-10 | New furan derivative and process for its preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2111557A1 DE2111557A1 (de) | 1971-09-23 |
| DE2111557B2 DE2111557B2 (de) | 1979-08-02 |
| DE2111557C3 true DE2111557C3 (de) | 1980-04-24 |
Family
ID=9986104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2111557A Expired DE2111557C3 (de) | 1970-03-10 | 1971-03-10 | 1 -(3-SuIfamoyl-4-chlor-benzamido) -3-(2-furyl)-pyrrolidin und ein Verfahren zu dessen Herstellung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3729484A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS4829223B2 (cg-RX-API-DMAC10.html) |
| AT (1) | AT299181B (cg-RX-API-DMAC10.html) |
| CA (1) | CA935167A (cg-RX-API-DMAC10.html) |
| CH (1) | CH536318A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2111557C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK125397B (cg-RX-API-DMAC10.html) |
| FR (1) | FR2085689B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1280393A (cg-RX-API-DMAC10.html) |
| IE (1) | IE34965B1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL142690B (cg-RX-API-DMAC10.html) |
| SE (1) | SE357968B (cg-RX-API-DMAC10.html) |
| ZA (2) | ZA71647B (cg-RX-API-DMAC10.html) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043874A (en) * | 1960-05-09 | 1962-07-10 | Parke Davis & Co | 4-halo-3-sulfamoylbenzoic acid derivatives and methods for producing same |
-
1970
- 1970-03-10 GB GB01430/70A patent/GB1280393A/en not_active Expired
-
1971
- 1971-02-02 ZA ZA710647A patent/ZA71647B/xx unknown
- 1971-02-02 ZA ZA710657A patent/ZA71657B/xx unknown
- 1971-02-09 NL NL717101661A patent/NL142690B/xx unknown
- 1971-02-15 DK DK66071AA patent/DK125397B/da unknown
- 1971-02-19 US US00117053A patent/US3729484A/en not_active Expired - Lifetime
- 1971-02-23 AT AT152771A patent/AT299181B/de not_active IP Right Cessation
- 1971-02-23 IE IE224/71A patent/IE34965B1/xx unknown
- 1971-03-03 JP JP46011230A patent/JPS4829223B2/ja not_active Expired
- 1971-03-05 FR FR7107595A patent/FR2085689B1/fr not_active Expired
- 1971-03-05 CA CA107045A patent/CA935167A/en not_active Expired
- 1971-03-08 SE SE02945/71A patent/SE357968B/xx unknown
- 1971-03-10 CH CH354171A patent/CH536318A/fr not_active IP Right Cessation
- 1971-03-10 DE DE2111557A patent/DE2111557C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK125397B (da) | 1973-02-12 |
| ZA71657B (en) | 1971-10-27 |
| DE2111557A1 (de) | 1971-09-23 |
| FR2085689B1 (cg-RX-API-DMAC10.html) | 1974-08-02 |
| IE34965L (en) | 1971-09-10 |
| NL142690B (nl) | 1974-07-15 |
| AT299181B (de) | 1972-06-12 |
| JPS4829223B2 (cg-RX-API-DMAC10.html) | 1973-09-08 |
| ZA71647B (en) | 1971-12-29 |
| FR2085689A1 (cg-RX-API-DMAC10.html) | 1971-12-31 |
| DE2111557B2 (de) | 1979-08-02 |
| CH536318A (fr) | 1973-04-30 |
| US3729484A (en) | 1973-04-24 |
| CA935167A (en) | 1973-10-09 |
| SE357968B (cg-RX-API-DMAC10.html) | 1973-07-16 |
| GB1280393A (en) | 1972-07-05 |
| NL7101661A (cg-RX-API-DMAC10.html) | 1971-09-14 |
| IE34965B1 (en) | 1975-10-01 |
| JPS462277A (cg-RX-API-DMAC10.html) | 1971-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |