GB1307539A - Thiourea derivatives - Google Patents
Thiourea derivativesInfo
- Publication number
- GB1307539A GB1307539A GB3083470A GB1307539DA GB1307539A GB 1307539 A GB1307539 A GB 1307539A GB 3083470 A GB3083470 A GB 3083470A GB 1307539D A GB1307539D A GB 1307539DA GB 1307539 A GB1307539 A GB 1307539A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- thiourea
- phthalimidobutyl
- thiazole
- butyl
- 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
- 150000003585 thioureas Chemical class 0.000 title abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ZLHYTYUSNRCNNJ-UHFFFAOYSA-N 2-[4-(1,3-thiazol-2-yl)butyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC1=NC=CS1 ZLHYTYUSNRCNNJ-UHFFFAOYSA-N 0.000 abstract 1
- YBWXSDDZFNMRJS-UHFFFAOYSA-N 2-[4-(1h-1,2,4-triazol-5-yl)butyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC=1N=CNN=1 YBWXSDDZFNMRJS-UHFFFAOYSA-N 0.000 abstract 1
- ZYWIGJGKLOVOQQ-UHFFFAOYSA-N 2-[4-(5-sulfanylidene-3,4-dihydro-1,2,4-triazol-3-yl)butyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC1NC(=S)N=N1 ZYWIGJGKLOVOQQ-UHFFFAOYSA-N 0.000 abstract 1
- YOCBHDSNVUDZDP-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)pentanethioamide Chemical compound C1=CC=C2C(=O)N(C(CCC(N)=S)C)C(=O)C2=C1 YOCBHDSNVUDZDP-UHFFFAOYSA-N 0.000 abstract 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003943 azolyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1307539 Thiourea derivatives SMITH KLINE & FRENCH LABORATORIES Ltd 22 June 1971 [25 June 1970 15 Oct 1970 22 Jan 1971] 30834/70 49007/70 and 2918/71 Heading C2C [Also in Division A5] Therapeutic compounds (II) (including salts thereof) where A is such that the cyclic group is an unsaturated heterocycle (the bond joining the carbon and nitrogen atoms shown can be a double bond), e.g. pyridine, imidazole, 1,2,4- triazole or thiazole, X is H, alkyl, halogen or alkylthio, n is 3 to 6 and R is H, alkyl or optionally substituted aroyl or aralkyl (but not benzyl), of which N-methyl-N<SP>1</SP>- {4- (4[5]-imid. azolyl)butyl}thiourea, N- methyl-N<SP>1</SP>-{ 4- (4-bro - mo-5-imidazolyl)-butyl}thiourea and N-methyl- N<SP>1</SP>-{4-(2-thiazolyl)butyl}thiourea are novel, are made, e.g., by interacting compounds (IV) and RNCS. The following compounds are also prepared:- p - hydroxyphen ethyl isothiocyanate, -1{5 - - (phthalimidovaleroyl) }thiosemicarbazide, 3- (4- phthalimidobutyl) - 1,2,4 - triazoline - 5 - thione, 3 - (4 - phthalimidobutyl) - 1,2,4 - triazole, 4 - phthalimido - thiovaleramide, 2 - (4 - phthalimidobutyl)thiazole, 4 - methyl - 5 - (21 - thienyl)- imidazole and its nitrate salt, 4- methyl -5-(5<SP>1</SP> nitro-2<SP>1</SP>-thienyl)thiazole and salts of (IV).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3083470 | 1970-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1307539A true GB1307539A (en) | 1973-02-21 |
Family
ID=10313874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3083470A Expired GB1307539A (en) | 1970-06-25 | 1970-06-25 | Thiourea derivatives |
Country Status (3)
| Country | Link |
|---|---|
| CY (1) | CY857A (en) |
| GB (1) | GB1307539A (en) |
| ZA (1) | ZA713549B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128658A (en) | 1976-08-04 | 1978-12-05 | Allen & Hanburys Limited | Aminoalkyl furan derivatives |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4165377A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
| EP0020173A1 (en) * | 1979-06-04 | 1980-12-10 | Merck & Co. Inc. | Imidazole guanidines, their preparation and compositions containing them |
| US4239769A (en) | 1977-05-17 | 1980-12-16 | Allen & Hanburys Limited | Pharmacologically active compounds |
| GB2191693A (en) * | 1986-06-18 | 1987-12-23 | Frederick Jacob Bloomfield | Anti-inflammatory agents |
| JP2012508249A (en) * | 2008-11-06 | 2012-04-05 | ムスク ファウンデーション フォー リサーチ デベロップメント | Lysosomal affinity inhibitors of acid ceramidase |
-
1970
- 1970-06-25 GB GB3083470A patent/GB1307539A/en not_active Expired
-
1971
- 1971-06-02 ZA ZA713549A patent/ZA713549B/en unknown
- 1971-06-22 CY CY857A patent/CY857A/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128658A (en) | 1976-08-04 | 1978-12-05 | Allen & Hanburys Limited | Aminoalkyl furan derivatives |
| US4255440A (en) | 1976-08-04 | 1981-03-10 | Allen & Hanburys Limited | Furan derivatives having selective action on histamine receptors |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4165377A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
| US4234735A (en) | 1977-04-20 | 1980-11-18 | Imperial Chemical Industries Limited | Guanidino imidazoles and thiazoles |
| US4262126A (en) | 1977-04-20 | 1981-04-14 | Imperial Chemical Industries Limited | Guanidine derivatives of imidazoles and thiazoles |
| US4239769A (en) | 1977-05-17 | 1980-12-16 | Allen & Hanburys Limited | Pharmacologically active compounds |
| EP0020173A1 (en) * | 1979-06-04 | 1980-12-10 | Merck & Co. Inc. | Imidazole guanidines, their preparation and compositions containing them |
| GB2191693A (en) * | 1986-06-18 | 1987-12-23 | Frederick Jacob Bloomfield | Anti-inflammatory agents |
| GB2191693B (en) * | 1986-06-18 | 1991-01-09 | Frederick Jacob Bloomfield | 5-lipoxygenase pathway inhibitors. |
| JP2012508249A (en) * | 2008-11-06 | 2012-04-05 | ムスク ファウンデーション フォー リサーチ デベロップメント | Lysosomal affinity inhibitors of acid ceramidase |
Also Published As
| Publication number | Publication date |
|---|---|
| CY857A (en) | 1976-09-10 |
| ZA713549B (en) | 1972-01-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |