GB1023205A - -triazino(5,6-6) indoles - Google Patents
-triazino(5,6-6) indolesInfo
- Publication number
- GB1023205A GB1023205A GB36551/63A GB3655163A GB1023205A GB 1023205 A GB1023205 A GB 1023205A GB 36551/63 A GB36551/63 A GB 36551/63A GB 3655163 A GB3655163 A GB 3655163A GB 1023205 A GB1023205 A GB 1023205A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- cyclizing
- optionally substituted
- compound
- 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
- 150000002475 indoles Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- VVICLQXCPOEFTM-UHFFFAOYSA-N 1,2,4-triazole-3,4-diamine Chemical compound NC1=NN=CN1N VVICLQXCPOEFTM-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises imidazo, pyrimido and triazolo-as-triazino-(5,6-b)-indoles of the formula <FORM:1023205/C2/1> wherein R is H or an alkyl or aralkyl group, X is a radical of the formula <FORM:1023205/C2/2> wherein R1 is H, OH, alkyl or phenyl, optionally substituted by one or more halogen atoms and/or one or more alkyl groups and their acid addition and quaternary ammonium salts and the preparation thereof (wherein X is -CR1= N-) by condensing isatin with a 3,4-diamino-1,2,4-triazole of the formula <FORM:1023205/C2/3> or by cyclizing a compound of the formula <FORM:1023205/C2/4> with urea or a carboxylic acid R2COOH, where R2 is H, alkyl or phenyl optionally substituted by one or more halogen atoms and/or one or more alkyl radicals; or (where X is -CH2-CH2CH2-or -CH2.CH2-) by cyclizing a compound of the formula <FORM:1023205/C2/5> with a cyclizing agent, e.g. POCl3. Pharmaceutical compositions having antiviral or antibacterial properties comprise the products of the invention together with a pharmaceutical carrier therefor. The compositions may be formulated as tablets, capsules, suppositories and solutions for injection.
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36551/63A GB1023205A (en) | 1963-09-17 | 1963-09-17 | -triazino(5,6-6) indoles |
| GB3519064D GB1023720A (en) | 1963-09-17 | 1963-09-17 | as-triazino (5,6-b)indoles |
| DE19641645935 DE1645935A1 (en) | 1963-09-17 | 1964-09-15 | Process for the preparation of as-triazino (5,6-b) indoles |
| DE19641445454 DE1445454A1 (en) | 1963-09-17 | 1964-09-15 | 3-Mercapto-as-triazino (5,6-b) indoles and process for their preparation |
| DE19641445453 DE1445453C (en) | 1963-09-17 | 1964-09-15 | s-Triazolo square bracket to 4, 3, -2,3 square bracket to -as-triazino square bracket to 5,6-square bracket to indole, process for their preparation and medicinal products |
| NL646410715A NL139235B (en) | 1963-09-17 | 1964-09-15 | PROCESS FOR THE PREPARATION OF A MEDICINAL PRODUCT WITH AN ANTIVIRUS ACTION AND SUITABLE THERAPEUTICALLY EFFECTIVE HETEROCYCLICAL COMPOUNDS. |
| US396721A US3312699A (en) | 1963-09-17 | 1964-09-15 | Asymmetric triazino indoles |
| DE19641645936 DE1645936A1 (en) | 1963-09-17 | 1964-09-15 | Process for the preparation of basic substituted as-triazino (5,6-b) indoles |
| BE653089D BE653089A (en) | 1963-09-17 | 1964-09-15 | |
| DE19641645934 DE1645934A1 (en) | 1963-09-17 | 1964-09-15 | Imidazo- or pyrimidino-as-triazino (5,6-b) indoles and processes for their preparation |
| BE653091D BE653091A (en) | 1963-09-17 | 1964-09-15 | |
| FR988258A FR1455036A (en) | 1963-09-17 | 1964-09-16 | Process for the preparation of new heterocyclic compounds |
| FR988257A FR3963M (en) | 1963-09-17 | 1964-09-16 | |
| NL6410823A NL6410823A (en) | 1963-09-17 | 1964-09-17 | |
| FR988451A FR3964M (en) | 1963-09-17 | 1964-09-17 | |
| FR1588752D FR1588752A (en) | 1963-09-17 | 1964-09-17 | |
| US745124A US3466281A (en) | 1963-09-17 | 1968-07-16 | As-triazino(5,6-b)indoles |
| US745126A US3467657A (en) | 1963-09-17 | 1968-07-16 | As-triazino(5,6-b)indoles |
| US745129A US3466282A (en) | 1963-09-17 | 1968-07-16 | As-triazino(5,6-b)indoles |
| US745086A US3493571A (en) | 1963-09-17 | 1968-07-16 | As-triazino(5,6-b)indoles |
| US745089A US3510482A (en) | 1963-09-17 | 1968-07-16 | As-triazino(5,6-b)-3-amino indoles |
| US74588*[A US3493569A (en) | 1963-09-17 | 1968-07-16 | 3-aminoalkylthio-as-triazino(5,6-b)-indoles |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36551/63A GB1023205A (en) | 1963-09-17 | 1963-09-17 | -triazino(5,6-6) indoles |
| GB716964 | 1964-02-20 | ||
| GB716864 | 1964-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1023205A true GB1023205A (en) | 1966-03-23 |
Family
ID=27254975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36551/63A Expired GB1023205A (en) | 1963-09-17 | 1963-09-17 | -triazino(5,6-6) indoles |
Country Status (5)
| Country | Link |
|---|---|
| BE (2) | BE653089A (en) |
| DE (1) | DE1445454A1 (en) |
| FR (4) | FR1455036A (en) |
| GB (1) | GB1023205A (en) |
| NL (2) | NL139235B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452013A (en) * | 1964-08-27 | 1969-06-24 | Allen & Hanburys Ltd | As-triazino(5,6-b)indoles |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3466282A (en) * | 1963-09-17 | 1969-09-09 | Allen & Hanburys Ltd | As-triazino(5,6-b)indoles |
| US3453276A (en) * | 1966-10-06 | 1969-07-01 | Smithkline Corp | Triazinoindole compounds |
| US3480628A (en) * | 1967-12-22 | 1969-11-25 | Smithkline Corp | 3-chlorotriazinoindoles |
| US7037909B2 (en) | 2003-07-02 | 2006-05-02 | Sugen, Inc. | Tetracyclic compounds as c-Met inhibitors |
-
1963
- 1963-09-17 GB GB36551/63A patent/GB1023205A/en not_active Expired
-
1964
- 1964-09-15 BE BE653089D patent/BE653089A/xx unknown
- 1964-09-15 BE BE653091D patent/BE653091A/xx unknown
- 1964-09-15 DE DE19641445454 patent/DE1445454A1/en active Pending
- 1964-09-15 NL NL646410715A patent/NL139235B/en unknown
- 1964-09-16 FR FR988258A patent/FR1455036A/en not_active Expired
- 1964-09-16 FR FR988257A patent/FR3963M/fr not_active Expired
- 1964-09-17 FR FR1588752D patent/FR1588752A/fr not_active Expired
- 1964-09-17 NL NL6410823A patent/NL6410823A/xx unknown
- 1964-09-17 FR FR988451A patent/FR3964M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452013A (en) * | 1964-08-27 | 1969-06-24 | Allen & Hanburys Ltd | As-triazino(5,6-b)indoles |
Also Published As
| Publication number | Publication date |
|---|---|
| FR3964M (en) | 1966-02-28 |
| FR1588752A (en) | 1970-03-16 |
| DE1445453A1 (en) | 1968-12-19 |
| FR3963M (en) | 1966-02-28 |
| NL139235B (en) | 1973-07-16 |
| NL6410715A (en) | 1965-03-18 |
| BE653091A (en) | 1964-12-31 |
| BE653089A (en) | 1964-12-31 |
| FR1455036A (en) | 1966-04-01 |
| DE1445454A1 (en) | 1968-12-19 |
| NL6410823A (en) | 1965-03-18 |
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