GB1397645A - Aza-benzimidazoles - Google Patents
Aza-benzimidazolesInfo
- Publication number
- GB1397645A GB1397645A GB3940272A GB3940272A GB1397645A GB 1397645 A GB1397645 A GB 1397645A GB 3940272 A GB3940272 A GB 3940272A GB 3940272 A GB3940272 A GB 3940272A GB 1397645 A GB1397645 A GB 1397645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- chloropyridine
- amino
- carbethoxyamino
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QEIRYIILFUVXAM-UHFFFAOYSA-N 6-chloropyridine-2,3-diamine Chemical compound NC1=CC=C(Cl)N=C1N QEIRYIILFUVXAM-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- KNOJSVBRYKBZNV-UHFFFAOYSA-N 3-N-benzyl-6-chloropyridine-2,3-diamine Chemical compound NC1=NC(=CC=C1NCC1=CC=CC=C1)Cl KNOJSVBRYKBZNV-UHFFFAOYSA-N 0.000 abstract 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 abstract 1
- FOGGQBVTIHSOGZ-UHFFFAOYSA-N 6-ethoxy-3-nitropyridin-2-amine Chemical compound CCOC1=CC=C([N+]([O-])=O)C(N)=N1 FOGGQBVTIHSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- NJECMUXVWUOITC-UHFFFAOYSA-N ethyl N-(2-amino-6-chloropyridin-3-yl)carbamate Chemical compound NC1=NC(=CC=C1NC(=O)OCC)Cl NJECMUXVWUOITC-UHFFFAOYSA-N 0.000 abstract 1
- LCROEPPBRIVGHJ-UHFFFAOYSA-N ethyl N-(2-amino-6-ethoxypyridin-3-yl)carbamate Chemical compound NC1=NC(=CC=C1NC(=O)OCC)OCC LCROEPPBRIVGHJ-UHFFFAOYSA-N 0.000 abstract 1
- IJBPNYZFBXXAPL-UHFFFAOYSA-N ethyl n-(2,6-diaminopyridin-3-yl)carbamate Chemical compound CCOC(=O)NC1=CC=C(N)N=C1N IJBPNYZFBXXAPL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 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
- C07D213/60—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 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1397645 Pyrido-imidazoles DEUTSCHE GOLDUND SILBER-SCHEIDEANSTALT 24 Aug 1972 [26 Aug 1971] 39402/72 Heading C2C Novel compounds (I) (including salts thereof) in which R<SP>1</SP> represents a chlorine or bromine atom, R<SP>2</SP> represents a hydrogen atom or a straight chain alkyl group with 1-6 carbon atoms, R<SP>3</SP> represents a hydrogen atom, a straight chain alkyl group with 1-6 carbon atoms, benzyl or represents the group CH 2 -COOH, and Y is a hydroxy group, a mercapto group, a benzyl amino group, a straight chain alkyl-mercapto group with 1-6 carbon atoms, a #-hydroxyethylamino group, a phenylamino group, a straight chain alkyl group with 1-6 carbon atoms, benzyl or the group -SCH 2 -COOH, are made by standard methods. The following compounds are also prepared: 2- amino-3-nitro-6-ethoxypyridine, 2-amino-3-carbethoxyamino-6-ethoxypyridine, 2,6-diamino-3- carbethoxyamino-pyridine. HCl, 2,3-diamino-6- chloropyridine. HCl, 2-amino-3-carbethoxyamino- 6-chloropyridine. HCl, the Schiffs base of 2,3- diamino-6-chloropyridine and benzaldehyde, 2- amino-3-benzylamino-6-chloropyridine, 2-hydroxy- and -methoxy-3-nitro-6-chloropyridine and 2 - amino - 3 - (N - benzyl) - carbethoxyamino - 6- chloropyridine. Pharmaceutical preparations contain (I) as active ingredient and are administered orally, parenterally or topically.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT748871A AT315831B (en) | 1971-08-26 | 1971-08-26 | Process for the preparation of new 4-aza-benzimidazole derivatives and their salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1397645A true GB1397645A (en) | 1975-06-11 |
Family
ID=3596529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3940272A Expired GB1397645A (en) | 1971-08-26 | 1972-08-24 | Aza-benzimidazoles |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS4832898A (en) |
| AR (1) | AR199879A1 (en) |
| AT (1) | AT315831B (en) |
| AU (1) | AU461671B2 (en) |
| BE (1) | BE788065A (en) |
| BR (1) | BR7205845A (en) |
| CA (1) | CA979907A (en) |
| CH (1) | CH592660A5 (en) |
| DD (1) | DD99580A5 (en) |
| DE (1) | DE2241575A1 (en) |
| ES (1) | ES405982A1 (en) |
| FR (1) | FR2150820B1 (en) |
| GB (1) | GB1397645A (en) |
| HU (1) | HU166382B (en) |
| IL (1) | IL40080A (en) |
| NL (1) | NL7211407A (en) |
| SU (1) | SU557758A3 (en) |
| YU (1) | YU34897B (en) |
| ZA (1) | ZA725868B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005318A1 (en) * | 1978-04-03 | 1979-11-14 | Janssen Pharmaceutica N.V. | N-Heterocyclyl-4-piperidinamines, methods for their preparation, pharmaceutical compositions comprising them, intermediates therefor, and method for the preparation of the intermediates |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4588722A (en) * | 1984-01-09 | 1986-05-13 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives |
| US4772600A (en) * | 1986-06-09 | 1988-09-20 | A. H. Robins Company, Inc. | Fused imidazoheterocyclic compounds and pharmaceutical compositions |
| JP2679745B2 (en) * | 1989-06-29 | 1997-11-19 | 明治製菓株式会社 | Azole derivatives and antiulcer agents containing them as active ingredients |
| US5200407A (en) * | 1989-06-29 | 1993-04-06 | Meiji Seika Kaburhiki Kaisha | Azole derivatives and anti-ulcerative composition containing same |
| AU748849B2 (en) | 1997-09-26 | 2002-06-13 | Zentaris Gmbh | Azabenzimidazole-based compounds for modulating serine/threonine protein kinase function |
| US8227603B2 (en) | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| JP5249217B2 (en) | 2006-08-02 | 2013-07-31 | サイトキネティクス・インコーポレーテッド | Specific chemicals, compositions and methods |
| WO2008121333A1 (en) * | 2007-03-30 | 2008-10-09 | Cytokinetics, Incorporated | Certain chemical entities, compositions and methods |
| EP2707373A1 (en) | 2011-05-10 | 2014-03-19 | Bayer Intellectual Property GmbH | Bicyclic (thio)carbonylamidines |
| EP2731611B1 (en) | 2011-07-13 | 2019-09-18 | Cytokinetics, Inc. | Combination therapie for als |
| EP3495366A1 (en) * | 2011-07-15 | 2019-06-12 | Shionogi & Co., Ltd | Azabenzimidazole derivative having ampk-activating activity |
-
0
- BE BE788065D patent/BE788065A/en unknown
-
1971
- 1971-08-26 AT AT748871A patent/AT315831B/en not_active IP Right Cessation
-
1972
- 1972-07-26 DD DD164684A patent/DD99580A5/xx unknown
- 1972-08-09 YU YU2041/72A patent/YU34897B/en unknown
- 1972-08-09 IL IL40080A patent/IL40080A/en unknown
- 1972-08-14 CH CH1201872A patent/CH592660A5/xx not_active IP Right Cessation
- 1972-08-18 SU SU1821216A patent/SU557758A3/en active
- 1972-08-19 ES ES405982A patent/ES405982A1/en not_active Expired
- 1972-08-21 NL NL7211407A patent/NL7211407A/xx not_active Application Discontinuation
- 1972-08-22 FR FR7229915A patent/FR2150820B1/fr not_active Expired
- 1972-08-24 DE DE2241575A patent/DE2241575A1/en active Pending
- 1972-08-24 GB GB3940272A patent/GB1397645A/en not_active Expired
- 1972-08-25 BR BR5845/72A patent/BR7205845A/en unknown
- 1972-08-25 JP JP47085203A patent/JPS4832898A/ja active Pending
- 1972-08-25 ZA ZA725868A patent/ZA725868B/en unknown
- 1972-08-25 AU AU45981/72A patent/AU461671B2/en not_active Expired
- 1972-08-25 HU HUDE789A patent/HU166382B/hu unknown
- 1972-08-25 CA CA150,204A patent/CA979907A/en not_active Expired
- 1972-08-28 AR AR243765A patent/AR199879A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005318A1 (en) * | 1978-04-03 | 1979-11-14 | Janssen Pharmaceutica N.V. | N-Heterocyclyl-4-piperidinamines, methods for their preparation, pharmaceutical compositions comprising them, intermediates therefor, and method for the preparation of the intermediates |
Also Published As
| Publication number | Publication date |
|---|---|
| AU461671B2 (en) | 1975-06-05 |
| FR2150820A1 (en) | 1973-04-13 |
| DE2241575A1 (en) | 1973-03-08 |
| IL40080A (en) | 1975-12-31 |
| IL40080A0 (en) | 1972-10-29 |
| HU166382B (en) | 1975-03-28 |
| CH592660A5 (en) | 1977-10-31 |
| NL7211407A (en) | 1973-02-28 |
| FR2150820B1 (en) | 1975-10-17 |
| JPS4832898A (en) | 1973-05-02 |
| ES405982A1 (en) | 1975-09-16 |
| SU557758A3 (en) | 1977-05-05 |
| BR7205845A (en) | 1976-05-04 |
| AU4598172A (en) | 1974-02-28 |
| AT315831B (en) | 1974-06-10 |
| YU204172A (en) | 1979-10-31 |
| CA979907A (en) | 1975-12-16 |
| BE788065A (en) | 1973-02-26 |
| YU34897B (en) | 1980-04-30 |
| DD99580A5 (en) | 1973-08-12 |
| ZA725868B (en) | 1973-05-30 |
| AR199879A1 (en) | 1974-10-08 |
| BR7205845D0 (en) | 1973-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1397645A (en) | Aza-benzimidazoles | |
| GB940596A (en) | ª -hydrazino acids | |
| GB1147379A (en) | 4-alkyl-dialkoxy-ª‡-methylphenethylamines and pharmacologically acceptable salts | |
| ES447010A1 (en) | Anti-diarrheal compounds | |
| GB1456627A (en) | Pyridobenzodiazepinones | |
| GB1427090A (en) | Fused indanone derivatives | |
| GB1415471A (en) | Phenylethylamine derivatives | |
| GB1377356A (en) | Tetrahydronaphthalene derivatives useful as pharmaceuticals | |
| GB1256723A (en) | ||
| GB1495778A (en) | Hexahydroazepines | |
| ES419381A1 (en) | Derivatives of 2-amino-(1,2,3,4-tetrahydronaphthalene), the preparation and use thereof | |
| GB1373367A (en) | Hydroxyalkyl substituted 4,5-dihydropyridazin 2h-3-ones | |
| GB1084152A (en) | ||
| GB1272606A (en) | Imidazolinyl benzalhydrazone and a process for its preparation | |
| GB1297035A (en) | ||
| GB1359560A (en) | Preparation of pyrrylsalicylic acid | |
| GB1415682A (en) | Amides and thioamides | |
| GB1394757A (en) | Lysino-calcium chloride | |
| GB1393228A (en) | 2-2-2-methyl-5-nitro-1-imidazolyl-ethyl-2-thiopseudoureas and related compounds | |
| GB1451389A (en) | Indolobenzazepines | |
| GB1275875A (en) | 3-amino-2-(3,4-disubstituted)bicyclo(2.2.2)octan-2-ols | |
| GB1178724A (en) | Novel Quaternary Compounds | |
| GB1310779A (en) | N-pyridylalkyl-beta-alkoxy-beta-trifluoromethylphenalkylamines | |
| GB1451320A (en) | Substituted oxazolines and thiazolines which are useful as tranquilizing agents | |
| GB1317848A (en) | N-thienylalkyl-beta-alkoxy-trifluoromethylphenalkylamines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |