GB1305549A - - Google Patents
Info
- Publication number
- GB1305549A GB1305549A GB1305549DA GB1305549A GB 1305549 A GB1305549 A GB 1305549A GB 1305549D A GB1305549D A GB 1305549DA GB 1305549 A GB1305549 A GB 1305549A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- formula
- imidazole
- prepared
- benzyl
- 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
- 238000006243 chemical reaction Methods 0.000 abstract 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 7
- 150000001412 amines Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- CSCKZXGPYQBZAW-UHFFFAOYSA-N 2-(6-chloro-4-oxohex-5-enyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC(=O)C=CCl)C(=O)C2=C1 CSCKZXGPYQBZAW-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- VVKSOQMOCOHGAM-UHFFFAOYSA-N 1-benzyl-2-(3-chloropropyl)imidazole Chemical compound ClCCCC1=NC=CN1CC1=CC=CC=C1 VVKSOQMOCOHGAM-UHFFFAOYSA-N 0.000 abstract 1
- PSKJVCNFAMZUFJ-UHFFFAOYSA-N 2-(5-bromo-4-oxopentyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC(=O)CBr)C(=O)C2=C1 PSKJVCNFAMZUFJ-UHFFFAOYSA-N 0.000 abstract 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 abstract 1
- OWLNROYRGWINFK-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)butanethioamide Chemical compound C1=CC=C2C(=O)N(C(CC(N)=S)C)C(=O)C2=C1 OWLNROYRGWINFK-UHFFFAOYSA-N 0.000 abstract 1
- HZOIHLSZMGDITC-UHFFFAOYSA-N 3-(1h-pyrazol-5-yl)propan-1-amine Chemical compound NCCCC1=CC=NN1 HZOIHLSZMGDITC-UHFFFAOYSA-N 0.000 abstract 1
- STXHPGKNMJVJKL-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)butanoyl chloride Chemical compound C1=CC=C2C(=O)N(CCCC(=O)Cl)C(=O)C2=C1 STXHPGKNMJVJKL-UHFFFAOYSA-N 0.000 abstract 1
- OJWDBEABFUDTAF-UHFFFAOYSA-N 4-(1-benzylimidazol-2-yl)butanenitrile Chemical compound N#CCCCC1=NC=CN1CC1=CC=CC=C1 OJWDBEABFUDTAF-UHFFFAOYSA-N 0.000 abstract 1
- JSDWILABWLKPBV-UHFFFAOYSA-N 4-[3-(1,3-thiazol-2-yl)propyl]isoindole-1,3-dione Chemical compound S1C(=NC=C1)CCCC1=C2C(C(=O)NC2=O)=CC=C1 JSDWILABWLKPBV-UHFFFAOYSA-N 0.000 abstract 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- UYAJHCFOMQJCDB-UHFFFAOYSA-N ethyl 3-(1-benzylimidazol-2-yl)propanoate Chemical compound CCOC(=O)CCC1=NC=CN1CC1=CC=CC=C1 UYAJHCFOMQJCDB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 150000002357 guanidines Chemical class 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1345072 | 1969-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1305549A true GB1305549A (en, 2012) | 1973-02-07 |
Family
ID=10023212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1305549D Expired GB1305549A (en, 2012) | 1969-10-29 | 1969-10-29 |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1305549A (en, 2012) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098898A (en) * | 1975-05-21 | 1978-07-04 | Smith Kline & French Laboratories Limited | Imidazolyl alkylguanidine compounds |
| US4165377A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4166856A (en) * | 1975-05-21 | 1979-09-04 | Smith Kline & French Laboratories Limited | Thiazole and isothiazole derivative as blockers of histamine H2 -receptors |
| US4192879A (en) * | 1975-05-21 | 1980-03-11 | Smith Kline & French Laboratories Limited | Imidazolyl alkylamino nitroethylene compounds |
| US4212875A (en) * | 1977-05-05 | 1980-07-15 | Smith Kline & French Laboratories Limited | Imidazolyl alkyl bisamidines |
| EP0020173A1 (en) * | 1979-06-04 | 1980-12-10 | Merck & Co. Inc. | Imidazole guanidines, their preparation and compositions containing them |
| US4242350A (en) | 1978-05-24 | 1980-12-30 | Imperial Chemical Industries Limited | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4315009A (en) | 1978-01-18 | 1982-02-09 | Imperial Chemical Industries Limited | Antisecretory guanidine derivatives and pharmaceutical compositions containing them |
| US4342765A (en) | 1979-01-18 | 1982-08-03 | Imperial Chemical Industries Limited | Guanidine derivatives and pharmaceutical compositions containing them |
| EP0397364A1 (en) * | 1989-05-09 | 1990-11-14 | Pfizer Inc. | Heterocyclic guanidines AS 5HT 3 Antagonists |
| FR2686084A1 (fr) * | 1992-01-10 | 1993-07-16 | Bioprojet Soc Civ | Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques. |
| USRE37303E1 (en) * | 1992-01-10 | 2001-07-31 | Institut National Del La Sante Et De La Recherche Medicale | Imidazole compounds and their therapeutic applications |
-
1969
- 1969-10-29 GB GB1305549D patent/GB1305549A/en not_active Expired
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166856A (en) * | 1975-05-21 | 1979-09-04 | Smith Kline & French Laboratories Limited | Thiazole and isothiazole derivative as blockers of histamine H2 -receptors |
| US4192879A (en) * | 1975-05-21 | 1980-03-11 | Smith Kline & French Laboratories Limited | Imidazolyl alkylamino nitroethylene compounds |
| US4098898A (en) * | 1975-05-21 | 1978-07-04 | Smith Kline & French Laboratories Limited | Imidazolyl alkylguanidine compounds |
| US4440775A (en) * | 1975-05-21 | 1984-04-03 | Smith Kline & French Laboratories Limited | Azolyl alkylthioureas and guanidines alkylaminonitroethylene compounds |
| US4333946A (en) | 1975-05-21 | 1982-06-08 | Smith Kline & French Laboratories Limited | Blocking histamine H2 -receptors with imidazolylalkyl guanidine derivatives |
| US4262126A (en) | 1977-04-20 | 1981-04-14 | Imperial Chemical Industries Limited | Guanidine derivatives of imidazoles and thiazoles |
| US4165377A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4234735A (en) | 1977-04-20 | 1980-11-18 | Imperial Chemical Industries Limited | Guanidino imidazoles and thiazoles |
| US4212875A (en) * | 1977-05-05 | 1980-07-15 | Smith Kline & French Laboratories Limited | Imidazolyl alkyl bisamidines |
| US4285952A (en) | 1977-05-05 | 1981-08-25 | Smith Kline & French Laboratories Limited | Pyridyl, thiazolyl and isothiazolyl alkyl bisamidines |
| US4372963A (en) | 1977-05-05 | 1983-02-08 | Smith Kline & French Laboratories Limited | Oxazolyl, isoxazolyl, triazolyl and thiadiazolyl alkyl bisamidines |
| US4315009A (en) | 1978-01-18 | 1982-02-09 | Imperial Chemical Industries Limited | Antisecretory guanidine derivatives and pharmaceutical compositions containing them |
| US4242350A (en) | 1978-05-24 | 1980-12-30 | Imperial Chemical Industries Limited | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4342765A (en) | 1979-01-18 | 1982-08-03 | Imperial Chemical Industries Limited | Guanidine derivatives and pharmaceutical compositions containing them |
| EP0020173A1 (en) * | 1979-06-04 | 1980-12-10 | Merck & Co. Inc. | Imidazole guanidines, their preparation and compositions containing them |
| EP0397364A1 (en) * | 1989-05-09 | 1990-11-14 | Pfizer Inc. | Heterocyclic guanidines AS 5HT 3 Antagonists |
| FR2686084A1 (fr) * | 1992-01-10 | 1993-07-16 | Bioprojet Soc Civ | Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques. |
| WO1993014070A3 (fr) * | 1992-01-10 | 1993-08-19 | Inst Nat Sante Rech Med | Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques |
| US5559113A (en) * | 1992-01-10 | 1996-09-24 | Institut National De La Sante Et De La Recherche Medicale | Imidazole compounds and their therapeutic applications |
| US5708171A (en) * | 1992-01-10 | 1998-01-13 | Institut National De La Sante Et De La Recherche Medicale | Imidazole derivatives for pharmaceutical use |
| USRE37303E1 (en) * | 1992-01-10 | 2001-07-31 | Institut National Del La Sante Et De La Recherche Medicale | Imidazole compounds and their therapeutic applications |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |