GB1380009A - Cyclic derivatives of 1,4-benzene disulphonamide - Google Patents
Cyclic derivatives of 1,4-benzene disulphonamideInfo
- Publication number
- GB1380009A GB1380009A GB3772072A GB3772072A GB1380009A GB 1380009 A GB1380009 A GB 1380009A GB 3772072 A GB3772072 A GB 3772072A GB 3772072 A GB3772072 A GB 3772072A GB 1380009 A GB1380009 A GB 1380009A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxypiperidinosulphonyl
- pharmaceutically acceptable
- alkylene
- formula
- oxo
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title 1
- 125000004122 cyclic group Chemical group 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003456 sulfonamides Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- JHYQFLQSZORYNF-UHFFFAOYSA-N 4-(4-methoxypiperidin-1-yl)sulfonyl-3-(trifluoromethyl)aniline Chemical compound C1CC(OC)CCN1S(=O)(=O)C1=CC=C(N)C=C1C(F)(F)F JHYQFLQSZORYNF-UHFFFAOYSA-N 0.000 abstract 1
- ZTVRDUIZRARMTM-UHFFFAOYSA-N 4-(4-methoxypiperidin-1-yl)sulfonyl-3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound COC1CCN(CC1)S(=O)(=O)C1=C(C=C(C=C1)S(=O)(=O)Cl)C(F)(F)F ZTVRDUIZRARMTM-UHFFFAOYSA-N 0.000 abstract 1
- QMPYGKMZUAEVSB-UHFFFAOYSA-N 4-methoxy-1-[4-nitro-2-(trifluoromethyl)phenyl]sulfonylpiperidine Chemical compound C1CC(OC)CCN1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1C(F)(F)F QMPYGKMZUAEVSB-UHFFFAOYSA-N 0.000 abstract 1
- ZEYSHALLPAKUHG-UHFFFAOYSA-N 4-methoxypiperidine Chemical compound COC1CCNCC1 ZEYSHALLPAKUHG-UHFFFAOYSA-N 0.000 abstract 1
- ICROHEDUOASYFB-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C(C(F)(F)F)=C1 ICROHEDUOASYFB-UHFFFAOYSA-N 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 230000002490 cerebral effect Effects 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- -1 cyclic amine Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 229940124549 vasodilator Drugs 0.000 abstract 1
- 239000003071 vasodilator agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1380009 Sulphonamides PFIZER Ltd 20 Aug 1973 [12 Aug 1972] 37720/72 Heading C2 The novel sulphonamides of general Formula I wherein R<SP>1</SP> represents F, Cl, Br or 3-CF 3 ; X represents O. S, -CH 2 - or a direct bond; y is 0, 1, or 2; m and n are independently 2 or 3 and when X is -CH 2 or a direct bond (R<SP>2</SP>) y represents up to two hydroxy or C 1-4 alkoxy groups or an oxo or C 1-4 alkylene dioxy group attached to the same or different carbon atoms of the heterocyclic ring provided that any oxygen atom in (R<SP>2</SP>) y is separated from the ring nitrogen atom by at least two carbon atoms or when X is O or S (R<SP>2</SP>) y represents up to two C 1-4 alkyl groups or a C 1-4 alkylene group attached to the heterocyclic ring, and their salts with pharmaceutically acceptable cations which may be prepared (except when (R<SP>2</SP>) y is an oxo group) by reacting, a compound of the Formula II with a cyclic amine of Formula III in a solvent such as acetone or dichloromethane, or if (R<SP>2</SP>) y is an oxo group by hydrolysis of the corresponding dialkyl or alkylene ketal, i.e. compounds in which (R<SP>2</SP>) y represents two alkoxy groups or an alkylene dioxy group. 1 - (4 - Methoxypiperidinosulphonyl)- 4- nitro - 2 - trifluoro - methyl benzene is prepared by reacting 4-methoxypiperidine with 4-nitro-2- trifluoromethylbenzene sulphonylchloride and is hydrogenated in methanol i.p.c. Pd. on charcoal to produce 4-(4-methoxypiperidinosulphonyl)-3- trifluoromethylaniline which is in turn diazotized and reacted with CuCl 2 and SO 2 in acetic acid to obtain 4 - (4 - methoxypiperidinosulphonyl)- 3-trifluoromethylbenzenesulphonyl chloride. Pharmaceutical compositions having cerebral vasodilator activity for oral or parenteral administration comprise a compound of the Formula I or pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier.
Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3772072A GB1380009A (en) | 1972-08-12 | 1972-08-12 | Cyclic derivatives of 1,4-benzene disulphonamide |
AT691573A AT331248B (en) | 1972-08-12 | 1973-08-07 | PROCESS FOR THE PREPARATION OF NEW CYCLIC, N-SUBSTITUTED 1,4-BENZENE DISULFONAMIDE DERIVATIVES AND THEIR SALT |
IE1344/73A IE38177B1 (en) | 1972-08-12 | 1973-08-07 | Cyclic derivatives of 1,4-benzene disulphonamide |
DE19732340010 DE2340010A1 (en) | 1972-08-12 | 1973-08-07 | CYCLIC, N-SUBSTITUTED 1,4BENZENE DISULFONAMIDE DERIVATIVES |
BE134373A BE803373A (en) | 1972-08-12 | 1973-08-08 | NEW DERIVATIVES OF 1,4-BENZENE-DISULFAMIDE AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
AU59084/73A AU5908473A (en) | 1972-08-12 | 1973-08-09 | 2 and 3 substituted-4-heterocyclic amino-sulfonyl benzene sulfonamides as cerebral vasodilators |
NL7311000.A NL162641C (en) | 1972-08-12 | 1973-08-09 | PROCESS FOR THE PREPARATION OF A PHARMACEUTICAL PREPARATION ON THE BASIS OF A 4- (HETEROCYCLOSULPHONYL) -BENZENE SULFONAMIDE SUBSTITUTED THEREFORE (PREPARED PREPARATIONS), PREPARED PREPARATIONS, AND PREPARED PREPARATIONS BENZENE SULPHONAMIDES. |
US386854A US3867390A (en) | 1972-08-12 | 1973-08-09 | 2 and 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides |
CA178,508A CA978945A (en) | 1972-08-12 | 1973-08-10 | Process for preparing 2 and 3 substituted-4-heterocyclic amino-sulfonyl benzene sulfonamides as cerebral vasodilators |
FR7329377A FR2195449B1 (en) | 1972-08-12 | 1973-08-10 | |
ZA735474A ZA735474B (en) | 1972-08-12 | 1973-08-10 | 2 and 3 substituted-4-heterocyclic aminosulfonyl benzene sulfonamides as vasodilators |
SE7310996A SE385008B (en) | 1972-08-12 | 1973-08-10 | METHOD OF PREPARING CYCLIC N-SUBSTITUTED DERIVATIVES OF 1,4- BENZENENISULPHONAMIDE DERIVATIVES |
LU68211A LU68211A1 (en) | 1972-08-12 | 1973-08-10 | |
ES417806A ES417806A1 (en) | 1972-08-12 | 1973-08-11 | 2 and 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides |
JP48090450A JPS59508B2 (en) | 1972-08-12 | 1973-08-11 | 2 3- Chikan -4- Fusokandiyouaminosulfonylbenzenesulfonamide |
IN1864/CAL/73A IN139006B (en) | 1972-08-12 | 1973-08-13 | |
US05/512,009 US3957796A (en) | 1972-08-12 | 1974-10-04 | 2 and 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides |
US05/512,008 US3974155A (en) | 1972-08-12 | 1974-10-04 | 2 AND 3-Substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides |
US05/512,012 US3932649A (en) | 1972-08-12 | 1974-10-04 | 2 And 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides as cerebral vasodilators |
JP56116291A JPS5857431B2 (en) | 1972-08-12 | 1981-07-24 | Method for producing cerebral vasodilator 2,3-substituted-4-heterocyclic aminosulfonylbenzenesulfonamide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3772072A GB1380009A (en) | 1972-08-12 | 1972-08-12 | Cyclic derivatives of 1,4-benzene disulphonamide |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1380009A true GB1380009A (en) | 1975-01-08 |
Family
ID=10398552
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3772072A Expired GB1380009A (en) | 1972-08-12 | 1972-08-12 | Cyclic derivatives of 1,4-benzene disulphonamide |
Country Status (16)
Country | Link |
---|---|
US (1) | US3867390A (en) |
JP (2) | JPS59508B2 (en) |
AT (1) | AT331248B (en) |
AU (1) | AU5908473A (en) |
BE (1) | BE803373A (en) |
CA (1) | CA978945A (en) |
DE (1) | DE2340010A1 (en) |
ES (1) | ES417806A1 (en) |
FR (1) | FR2195449B1 (en) |
GB (1) | GB1380009A (en) |
IE (1) | IE38177B1 (en) |
IN (1) | IN139006B (en) |
LU (1) | LU68211A1 (en) |
NL (1) | NL162641C (en) |
SE (1) | SE385008B (en) |
ZA (1) | ZA735474B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4450877A (en) * | 1977-11-03 | 1984-05-29 | Hoechst Aktiengesellschaft | Pharmaceutical preparations in solid unit dosage form |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070361A (en) * | 1977-04-21 | 1978-01-24 | E. R. Squibb & Sons, Inc. | Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof |
DE2720654A1 (en) * | 1977-05-07 | 1978-11-16 | Bayer Ag | AZOLYL ALKANOCARBONIC ACID DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS FUNGICIDES |
JPS5922023A (en) * | 1982-07-27 | 1984-02-04 | Hoya Corp | Beam splitter |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3165550A (en) * | 1960-06-29 | 1965-01-12 | Pfizer & Co C | N-substituted p-benzenedisulfonamides |
-
1972
- 1972-08-12 GB GB3772072A patent/GB1380009A/en not_active Expired
-
1973
- 1973-08-07 DE DE19732340010 patent/DE2340010A1/en not_active Ceased
- 1973-08-07 AT AT691573A patent/AT331248B/en not_active IP Right Cessation
- 1973-08-07 IE IE1344/73A patent/IE38177B1/en unknown
- 1973-08-08 BE BE134373A patent/BE803373A/en unknown
- 1973-08-09 AU AU59084/73A patent/AU5908473A/en not_active Expired
- 1973-08-09 US US386854A patent/US3867390A/en not_active Expired - Lifetime
- 1973-08-09 NL NL7311000.A patent/NL162641C/en not_active IP Right Cessation
- 1973-08-10 LU LU68211A patent/LU68211A1/xx unknown
- 1973-08-10 SE SE7310996A patent/SE385008B/en unknown
- 1973-08-10 ZA ZA735474A patent/ZA735474B/en unknown
- 1973-08-10 FR FR7329377A patent/FR2195449B1/fr not_active Expired
- 1973-08-10 CA CA178,508A patent/CA978945A/en not_active Expired
- 1973-08-11 JP JP48090450A patent/JPS59508B2/en not_active Expired
- 1973-08-11 ES ES417806A patent/ES417806A1/en not_active Expired
- 1973-08-13 IN IN1864/CAL/73A patent/IN139006B/en unknown
-
1981
- 1981-07-24 JP JP56116291A patent/JPS5857431B2/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4450877A (en) * | 1977-11-03 | 1984-05-29 | Hoechst Aktiengesellschaft | Pharmaceutical preparations in solid unit dosage form |
Also Published As
Publication number | Publication date |
---|---|
FR2195449A1 (en) | 1974-03-08 |
LU68211A1 (en) | 1975-05-21 |
CA978945A (en) | 1975-12-02 |
NL162641B (en) | 1980-01-15 |
IE38177B1 (en) | 1978-01-18 |
AU5908473A (en) | 1975-02-13 |
JPS5857431B2 (en) | 1983-12-20 |
IE38177L (en) | 1974-02-12 |
BE803373A (en) | 1974-02-08 |
JPS59508B2 (en) | 1984-01-07 |
US3867390A (en) | 1975-02-18 |
SE385008B (en) | 1976-05-31 |
JPS4985066A (en) | 1974-08-15 |
NL162641C (en) | 1980-06-16 |
JPS57131774A (en) | 1982-08-14 |
NL7311000A (en) | 1974-02-14 |
AT331248B (en) | 1976-08-10 |
IN139006B (en) | 1976-04-24 |
FR2195449B1 (en) | 1977-09-09 |
DE2340010A1 (en) | 1974-03-14 |
ES417806A1 (en) | 1976-03-01 |
ZA735474B (en) | 1974-08-28 |
ATA691573A (en) | 1975-11-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |