NO129476B - - Google Patents
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- Publication number
- NO129476B NO129476B NO02697/73A NO269773A NO129476B NO 129476 B NO129476 B NO 129476B NO 02697/73 A NO02697/73 A NO 02697/73A NO 269773 A NO269773 A NO 269773A NO 129476 B NO129476 B NO 129476B
- Authority
- NO
- Norway
- Prior art keywords
- radical
- general formula
- compounds
- alkyl radical
- compound
- Prior art date
Links
- -1 piperidyl- Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229940081974 saccharin Drugs 0.000 claims description 14
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 230000001882 diuretic effect Effects 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- HREJRPFXOLCYSA-UHFFFAOYSA-N 2,3-disulfamoylbenzoic acid Chemical compound S(N)(=O)(=O)C=1C(=C(C(=O)O)C=CC1)S(N)(=O)=O HREJRPFXOLCYSA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- 235000019204 saccharin Nutrition 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DDHZYEVPFSJSTO-UHFFFAOYSA-N ClC=1C=C2C(NS(=O)(=O)C2=CC1S(N)(=O)=O)=O Chemical compound ClC=1C=C2C(NS(=O)(=O)C2=CC1S(N)(=O)=O)=O DDHZYEVPFSJSTO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QURZKDMMFULGAQ-UHFFFAOYSA-N 5-chloro-2,4-disulfamoylbenzoic acid Chemical compound ClC=1C(=CC(=C(C(=O)O)C1)S(N)(=O)=O)S(N)(=O)=O QURZKDMMFULGAQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OMXSZBDLOAPYFT-UHFFFAOYSA-N 1,1,3-trioxo-1,2-benzothiazole-2-sulfonamide Chemical class S(N)(=O)(=O)N1S(=O)(=O)C2=CC=CC=C2C1=O OMXSZBDLOAPYFT-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- FRERWPYJIUVOKA-UHFFFAOYSA-N 2,4-disulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C(S(N)(=O)=O)=C1 FRERWPYJIUVOKA-UHFFFAOYSA-N 0.000 description 1
- OYGBYDIPUSWGFK-UHFFFAOYSA-N 5-nitro-1,1,3-trioxo-1,2-benzothiazole-6-sulfonamide Chemical compound [N+](=O)([O-])C=1C=C2C(NS(=O)(=O)C2=CC1S(N)(=O)=O)=O OYGBYDIPUSWGFK-UHFFFAOYSA-N 0.000 description 1
- CJDPETUNDLYYJZ-UHFFFAOYSA-N BrC=1C=C2C(NS(=O)(=O)C2=CC1S(N)(=O)=O)=O Chemical compound BrC=1C=C2C(NS(=O)(=O)C2=CC1S(N)(=O)=O)=O CJDPETUNDLYYJZ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- KCCAUFVYUOTNKE-UHFFFAOYSA-N ClC1=CC(=C(C(=O)O)C=C1S(N)(=O)=O)S(N)(=O)=O Chemical compound ClC1=CC(=C(C(=O)O)C=C1S(N)(=O)=O)S(N)(=O)=O KCCAUFVYUOTNKE-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BZCGWAXQDLXLQM-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O.ClP(Cl)(Cl)=O BZCGWAXQDLXLQM-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F11/00—Control or safety arrangements
- F24F11/70—Control systems characterised by their outputs; Constructional details thereof
- F24F11/72—Control systems characterised by their outputs; Constructional details thereof for controlling the supply of treated air, e.g. its pressure
- F24F11/74—Control systems characterised by their outputs; Constructional details thereof for controlling the supply of treated air, e.g. its pressure for controlling air flow rate or air velocity
- F24F11/76—Control systems characterised by their outputs; Constructional details thereof for controlling the supply of treated air, e.g. its pressure for controlling air flow rate or air velocity by means responsive to temperature, e.g. bimetal springs
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Ventilation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE10896/72A SE366107B (enExample) | 1972-08-22 | 1972-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129476B true NO129476B (enExample) | 1974-04-16 |
Family
ID=20293015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02697/73A NO129476B (enExample) | 1972-08-22 | 1973-06-29 |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2330042A1 (enExample) |
| FR (1) | FR2197150B3 (enExample) |
| NO (1) | NO129476B (enExample) |
| SE (1) | SE366107B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56146414A (en) * | 1980-04-11 | 1981-11-13 | Nippon Denso Co Ltd | Airconditioning control method for vehicle |
-
1972
- 1972-08-22 SE SE10896/72A patent/SE366107B/xx unknown
-
1973
- 1973-06-13 DE DE2330042A patent/DE2330042A1/de active Pending
- 1973-06-29 NO NO02697/73A patent/NO129476B/no unknown
- 1973-08-14 FR FR7329656A patent/FR2197150B3/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE366107B (enExample) | 1974-04-08 |
| FR2197150A1 (enExample) | 1974-03-22 |
| FR2197150B3 (enExample) | 1976-07-30 |
| DE2330042A1 (de) | 1974-03-14 |
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