DE2548283A1 - 1,2,4-benzothiadiazin-1,1-dioxidderivate - Google Patents
1,2,4-benzothiadiazin-1,1-dioxidderivateInfo
- Publication number
- DE2548283A1 DE2548283A1 DE19752548283 DE2548283A DE2548283A1 DE 2548283 A1 DE2548283 A1 DE 2548283A1 DE 19752548283 DE19752548283 DE 19752548283 DE 2548283 A DE2548283 A DE 2548283A DE 2548283 A1 DE2548283 A1 DE 2548283A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dioxide
- benzothiadiazine
- compound
- piperazinyl
- 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.)
- Withdrawn
Links
- BBNGVMNBBLPZIR-UHFFFAOYSA-N 4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)N=CNC2=C1 BBNGVMNBBLPZIR-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- JPZVJONKWYICFB-UHFFFAOYSA-N 7-chloro-3-(4-methylpiperazin-1-yl)-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C1CN(C)CCN1C1=NS(=O)(=O)C2=CC(Cl)=CC=C2N1 JPZVJONKWYICFB-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- SKQATQXQLBPNCC-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2S(=O)(=O)N1 SKQATQXQLBPNCC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 101150052863 THY1 gene Proteins 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
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- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002934 diuretic Substances 0.000 description 5
- 230000001882 diuretic effect Effects 0.000 description 5
- 229960002003 hydrochlorothiazide Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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 4
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- 230000003345 hyperglycaemic effect Effects 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- CCGOAQGXOPIWBI-UHFFFAOYSA-N 7-chloro-3-piperazin-1-yl-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound N1S(=O)(=O)C2=CC(Cl)=CC=C2N=C1N1CCNCC1 CCGOAQGXOPIWBI-UHFFFAOYSA-N 0.000 description 3
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- 230000036543 hypotension Effects 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 201000005857 malignant hypertension Diseases 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 239000003451 thiazide diuretic agent Substances 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12513574A JPS5152186A (en) | 1974-10-29 | 1974-10-29 | 77 kuroro 33 * 44 mechiru 11 piperajiniru * 2hh1*2*44 benzochiajiajin 1*11 jiokishidono seizoho |
JP50015050A JPS5191278A (en) | 1975-02-04 | 1975-02-04 | 33 * 44 mechiru 11 piperajiniru * 2hh1*2*44 benzochiajiajin 1*11 jiokishidono seizoho |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2548283A1 true DE2548283A1 (de) | 1976-05-06 |
Family
ID=26351120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752548283 Withdrawn DE2548283A1 (de) | 1974-10-29 | 1975-10-28 | 1,2,4-benzothiadiazin-1,1-dioxidderivate |
Country Status (6)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0906297B1 (en) * | 1996-06-21 | 2004-02-25 | Université de Liège | 1,2,4-benzothiadiazine derivatives, their preparation and use |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6900220B2 (en) * | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
AU2002359320A1 (en) * | 2001-10-29 | 2003-05-12 | Smithkline Beecham Corporation | Novel anit-infectives |
EP2208496A1 (en) * | 2004-08-25 | 2010-07-21 | Essentialis, Inc. | Pharmaceutical formulations of potassium ATP channel openers and uses thereof |
EP3545958B1 (en) | 2006-01-05 | 2024-07-10 | Essentialis, Inc. | Salts of potassium atp channel openers and uses thereof |
AU2008272923A1 (en) * | 2007-07-02 | 2009-01-08 | Essentialis, Inc. | Salts of potassium ATP channel openers and uses thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133918A (en) * | 1964-05-19 | Derivatives of | ||
US3269906A (en) * | 1966-08-30 | Imino-j,x-dihydro-l,z,x-benzothiadiazine- i,i-dioxides | ||
US3163644A (en) * | 1959-10-16 | 1964-12-29 | Ciba Geigy Corp | Derivatives of 2-h-1, 2, 4-benzo thiadiazine-1, 1-dioxide |
US3960854A (en) * | 1972-03-20 | 1976-06-01 | Merck & Co., Inc. | 7-Mercapto(or thio)-benzothiadiazine products |
US3957769A (en) * | 1973-11-23 | 1976-05-18 | E. R. Squibb & Sons, Inc. | 1,2,4-benzothiadiazines |
-
1975
- 1975-10-28 CA CA238,490A patent/CA1056827A/en not_active Expired
- 1975-10-28 DE DE19752548283 patent/DE2548283A1/de not_active Withdrawn
- 1975-10-28 ES ES442149A patent/ES442149A1/es not_active Expired
- 1975-10-28 US US05/626,042 patent/US4029780A/en not_active Expired - Lifetime
- 1975-10-29 GB GB44728/75A patent/GB1503180A/en not_active Expired
- 1975-10-29 FR FR7533023A patent/FR2289195A1/fr active Granted
Non-Patent Citations (3)
Title |
---|
J.Med.Chem., 11, 1968, 136-138 * |
J.Med.Chem., 15, 1972, 394-400 * |
Z: Dtsch. Apotheker Ztg., 117, 1977, S. 1368 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0906297B1 (en) * | 1996-06-21 | 2004-02-25 | Université de Liège | 1,2,4-benzothiadiazine derivatives, their preparation and use |
Also Published As
Publication number | Publication date |
---|---|
US4029780A (en) | 1977-06-14 |
FR2289195B1 (US07655688-20100202-C00086.png) | 1980-05-09 |
CA1056827A (en) | 1979-06-19 |
FR2289195A1 (fr) | 1976-05-28 |
GB1503180A (en) | 1978-03-08 |
ES442149A1 (es) | 1977-04-01 |
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8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
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8136 | Disposal/non-payment of the fee for publication/grant |