GB1253709A - Thiadiazole derivatives - Google Patents
Thiadiazole derivativesInfo
- Publication number
- GB1253709A GB1253709A GB2533369A GB2533369A GB1253709A GB 1253709 A GB1253709 A GB 1253709A GB 2533369 A GB2533369 A GB 2533369A GB 2533369 A GB2533369 A GB 2533369A GB 1253709 A GB1253709 A GB 1253709A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- optionally
- atom
- membered
- substituents selected
- 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
- 150000004867 thiadiazoles Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- 229910052799 carbon Inorganic materials 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000001424 substituent group Chemical group 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- -1 pyrrolidinyl Chemical group 0.000 abstract 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 238000001321 HNCO Methods 0.000 abstract 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000674 adrenergic antagonist Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,253,709. Thiadiazoles. CHARLES E. FROSST & CO. 19 May, 1969 [22 May, 1968; 21 April, 1969], No. 25333/69. Heading C2C. Compounds of the general formula (R = H, Cl, Br, C 1-5 alkyl or alkoxy, C 2-5 alkenyl, C 3-6 cycloalkyl, Y-X-Z (Y = C 1-4 alkyl optionally substituted by Ph or Ph having one or more substituents selected from halogen atoms and OH, C 1-3 alkyl and alkoxy groups; Z= C 1-2 alkyl; X=O, S), R<SP>51</SP> HNCO (R<SP>51</SP> = C 1-5 alkyl), Ph or Ph-(C 1-4 alkyl) optionally having one or more substituents selected from halogen atoms and C 1-3 alkyl and alkoxy groups attached to the ring, NR<SP>7</SP>R<SP>8</SP> (R<SP>7</SP> = H, C 1-4 alkyl, C 2-4 hydroxyalkyl R<SP>8</SP> = H, C 1-4 alkyl, C 2-4 hydroxyalkyl, Ph or NR<SP>7</SP>R<SP>8</SP> = 3-7 membered ring optionally having one or more substituents selected from OH, C 1-5 alkyl, C 1-3 hydroxyalkyl or R<SP>7</SP> and R<SP>8</SP> are joined through an O, N or S atom to form a 5-6 membered ring together with the N atom to which they are attached, optionally C 1-3 alkyl substituted), 5-6 membered heterocyclic ring linked through a carbon atom and having O, N or S as the hetero atom; R<SP>1,2,4</SP>=H, C 1-3 alkyl; R<SP>3</SP>=H, PhCO, C 2- 4 alkanoyl; R<SP>5</SP>=H, C 1-5 alkyl, Ph C 1-3 alkyl or C 2-5 alkanoyl; R<SP>6</SP>=C 1-20 alkyl, C 2-6 alkenyl or alkynyl optionally having one or more substituents selected from halogen atoms, OH, carboxy, (C 1-3 alkoxy) carbonyl, C 1-4 alkoxy and alkylthio, di-(C 1-3 alkyl) amino, pyrrolidinyl, piperazinyl, piperidinyl, morpholino, thiazolidinyl, thiazinyl, 5-6 membered heterocyclic rings attached through a nuclear carbon atom and having O, N or S as the hetero atom, Ph and PhO optionally having 1-3 substituents selected from halogen atoms, OH and C 1-3 alkoxy groups, Ph optionally substituted by C 1-3 alkyl, pyrrolidinyl, piperidinyl, C 3-6 cycloalkyl optionally substituted by C 1-3 alkyl or 5-6 membered N or O-containing ring, 5-6 membered heterocyclic ring containing O, N or S as the hetero atom and attached through a nuclear carbon atom and optionally substituted by C 1-3 alkyl or 5-6 membered N or O-containing heterocyclic ring, or NR<SP>5</SP>R<SP>6</SP>=4-6 membered ring which may contain in addition to but not adjacent to the N atom one or two different hetero atoms selected from O, S, N and which may be substituted by one or more C 1-3 alkyl radicals) and their salts are prepared by the following routes: optionally followed by esterification. The above compounds are #-adrenergic blocking agents and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73133368A | 1968-05-22 | 1968-05-22 | |
| US81809069A | 1969-04-21 | 1969-04-21 | |
| US17914571A | 1971-09-09 | 1971-09-09 | |
| US17914771A | 1971-09-09 | 1971-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1253709A true GB1253709A (en) | 1971-11-17 |
Family
ID=27497322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2533369A Expired GB1253709A (en) | 1968-05-22 | 1969-05-19 | Thiadiazole derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT289789B (en) |
| BE (1) | BE733390A (en) |
| CH (1) | CH560207A5 (en) |
| CY (1) | CY762A (en) |
| DE (1) | DE1925956C3 (en) |
| FR (1) | FR2009110A1 (en) |
| GB (1) | GB1253709A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034542A3 (en) * | 1980-02-19 | 1981-10-21 | Merck & Co. Inc. | S-(-)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)-oxy)-2-propanol pamoate for topical application in the treatment of elevated intraocular pressure |
| EP0105996A1 (en) * | 1982-10-15 | 1984-04-25 | Merck & Co. Inc. | Ophthalmic compositions for treating elevated intraocular pressure |
| US8338489B2 (en) | 2007-10-19 | 2012-12-25 | Université Victor Segalen—Bordeaux 2 | Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas |
| US8987262B2 (en) | 2007-10-19 | 2015-03-24 | Universite de Bordeaux | Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3475615D1 (en) * | 1983-02-03 | 1989-01-19 | Univ California | Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists |
| US4687873A (en) * | 1983-02-03 | 1987-08-18 | The Regents Of The University Of California | Derivatives of β-adrenergic antagonists |
| EP0414511A1 (en) * | 1989-08-22 | 1991-02-27 | Tosoh Corporation | Thiadiazole derivatives and herbicide compositions containing the same |
| US5482916A (en) * | 1989-08-22 | 1996-01-09 | Tosoh Corporation | Thiadiazole derivatives and herbicide compositions containing same |
| CA2120603A1 (en) * | 1991-10-11 | 1993-04-15 | Louis Desantis Jr. | Topical opthalmic compositions comprising 4-(3-substituted amino-2-hydroxypropoxy)-1,2,5-thiadiazoles and methods for their use |
| US5821371A (en) * | 1994-10-24 | 1998-10-13 | Eli Lilly And Comany | Heterocyclic compounds and their preparation and use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| US3419573A (en) * | 1965-10-15 | 1968-12-31 | Merck & Co Inc | 3-chloro-4-oxy-1,2,5-thiadiazoles, and a process for preparing same |
-
1969
- 1969-05-19 GB GB2533369A patent/GB1253709A/en not_active Expired
- 1969-05-21 CH CH135272A patent/CH560207A5/xx not_active IP Right Cessation
- 1969-05-21 AT AT483969A patent/AT289789B/en active
- 1969-05-21 DE DE19691925956 patent/DE1925956C3/en not_active Expired
- 1969-05-21 BE BE733390D patent/BE733390A/xx not_active IP Right Cessation
- 1969-05-22 FR FR6916642A patent/FR2009110A1/fr active Pending
-
1974
- 1974-11-01 CY CY76274A patent/CY762A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034542A3 (en) * | 1980-02-19 | 1981-10-21 | Merck & Co. Inc. | S-(-)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)-oxy)-2-propanol pamoate for topical application in the treatment of elevated intraocular pressure |
| EP0105996A1 (en) * | 1982-10-15 | 1984-04-25 | Merck & Co. Inc. | Ophthalmic compositions for treating elevated intraocular pressure |
| US8338489B2 (en) | 2007-10-19 | 2012-12-25 | Université Victor Segalen—Bordeaux 2 | Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas |
| US8987262B2 (en) | 2007-10-19 | 2015-03-24 | Universite de Bordeaux | Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas |
| US9173858B2 (en) | 2007-10-19 | 2015-11-03 | Universite de Bordeaux | Use of a beta blocker for the manufacture of a medicament for the treatment of hemangiomas |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1925956B2 (en) | 1979-11-22 |
| FR2009110A1 (en) | 1970-01-30 |
| BE733390A (en) | 1969-11-21 |
| DE1925956A1 (en) | 1969-11-27 |
| AT289789B (en) | 1971-05-10 |
| CH560207A5 (en) | 1975-03-27 |
| CY762A (en) | 1974-11-01 |
| DE1925956C3 (en) | 1980-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746D | Case decided by the comptroller (sect. 46(3)/1977) | ||
| PE20 | Patent expired after termination of 20 years |