GB1065964A - Substituted carbamyl aminotriazoles,their preparation and compositions containing them - Google Patents
Substituted carbamyl aminotriazoles,their preparation and compositions containing themInfo
- Publication number
- GB1065964A GB1065964A GB4650163A GB4650163A GB1065964A GB 1065964 A GB1065964 A GB 1065964A GB 4650163 A GB4650163 A GB 4650163A GB 4650163 A GB4650163 A GB 4650163A GB 1065964 A GB1065964 A GB 1065964A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triazole
- compounds
- amino
- aminotriazole
- reacting
- 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 3
- -1 acyclic hydrocarbon Chemical class 0.000 abstract 13
- 150000001875 compounds Chemical class 0.000 abstract 10
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003852 triazoles Chemical class 0.000 abstract 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 2
- WVZXERQNQLNDTH-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(1,2,4-triazol-1-yl)methanimine Chemical compound C1=CC(Cl)=CC=C1C=NN1N=CN=C1 WVZXERQNQLNDTH-UHFFFAOYSA-N 0.000 abstract 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 abstract 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- CVVWGMYRAAPXGZ-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylideneamino]-N,N-dimethyl-1,2,4-triazole-1-carboxamide Chemical compound CN(C(=O)N1N=C(N=C1)N=CC1=CC=C(C=C1)OC)C CVVWGMYRAAPXGZ-UHFFFAOYSA-N 0.000 abstract 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 abstract 1
- GINARBSIFVGEJO-UHFFFAOYSA-N 4-methyl-n-(1h-1,2,4-triazol-5-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC=NN1 GINARBSIFVGEJO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003434 antitussive agent Substances 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- APBBAQCENVXUHL-UHFFFAOYSA-N n,n-diethylethanamine;2,2,2-trifluoroacetic acid Chemical compound CCN(CC)CC.OC(=O)C(F)(F)F APBBAQCENVXUHL-UHFFFAOYSA-N 0.000 abstract 1
- JFNQRZQLFJSYLO-UHFFFAOYSA-N n,n-dimethyl-1h-1,2,4-triazol-5-amine Chemical compound CN(C)C1=NC=NN1 JFNQRZQLFJSYLO-UHFFFAOYSA-N 0.000 abstract 1
- CUBGIFZGVRKESN-UHFFFAOYSA-N n-(triazol-1-yl)acetamide Chemical compound CC(=O)NN1C=CN=N1 CUBGIFZGVRKESN-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical class CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 abstract 1
- HUUBMTMJIQHAEN-UHFFFAOYSA-N triazole-1,4-diamine Chemical compound NC1=CN(N)N=N1 HUUBMTMJIQHAEN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011782 vitamin Substances 0.000 abstract 1
- 229940088594 vitamin Drugs 0.000 abstract 1
- 229930003231 vitamin Natural products 0.000 abstract 1
- 235000013343 vitamin Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24263662A | 1962-12-06 | 1962-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1065964A true GB1065964A (en) | 1967-04-19 |
Family
ID=22915594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4650163A Expired GB1065964A (en) | 1962-12-06 | 1963-11-25 | Substituted carbamyl aminotriazoles,their preparation and compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT250953B (enrdf_load_stackoverflow) |
| CH (1) | CH458375A (enrdf_load_stackoverflow) |
| DE (1) | DE1470158A1 (enrdf_load_stackoverflow) |
| DK (1) | DK124261B (enrdf_load_stackoverflow) |
| GB (1) | GB1065964A (enrdf_load_stackoverflow) |
| LU (1) | LU44720A1 (enrdf_load_stackoverflow) |
| NL (1) | NL301383A (enrdf_load_stackoverflow) |
| NO (1) | NO115111B (enrdf_load_stackoverflow) |
| SE (1) | SE321684B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2189409A1 (enrdf_load_stackoverflow) * | 1972-06-19 | 1974-01-25 | Ciba Geigy Ag | |
| EP0710654A4 (en) * | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
| WO2002057240A1 (en) * | 2000-12-22 | 2002-07-25 | Ortho Mc Neil Pharmaceutical, Inc. | Substituted triazole diamine derivatives as kinase inhibitors |
-
0
- NL NL301383D patent/NL301383A/xx unknown
-
1963
- 1963-10-28 LU LU44720D patent/LU44720A1/xx unknown
- 1963-11-25 GB GB4650163A patent/GB1065964A/en not_active Expired
- 1963-11-30 DE DE19631470158 patent/DE1470158A1/de active Pending
- 1963-12-02 NO NO15107163A patent/NO115111B/no unknown
- 1963-12-05 DK DK567963A patent/DK124261B/da unknown
- 1963-12-05 SE SE1349763A patent/SE321684B/xx unknown
- 1963-12-05 CH CH1497863A patent/CH458375A/de unknown
- 1963-12-06 AT AT981163A patent/AT250953B/de active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2189409A1 (enrdf_load_stackoverflow) * | 1972-06-19 | 1974-01-25 | Ciba Geigy Ag | |
| EP0710654A4 (en) * | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
| WO2002057240A1 (en) * | 2000-12-22 | 2002-07-25 | Ortho Mc Neil Pharmaceutical, Inc. | Substituted triazole diamine derivatives as kinase inhibitors |
| US6924302B2 (en) | 2000-12-22 | 2005-08-02 | Ortho Mcneil Pharmaceutical, Inc. | Substituted triazole diamine derivatives as kinase inhibitors |
| CN100357278C (zh) * | 2000-12-22 | 2007-12-26 | 奥索-麦克尼尔药品公司 | 作为激酶抑制剂的取代的三唑二胺衍生物 |
| US7317031B2 (en) | 2000-12-22 | 2008-01-08 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted triazole diamine derivatives as kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470158A1 (de) | 1969-11-13 |
| AT250953B (de) | 1966-12-12 |
| NL301383A (enrdf_load_stackoverflow) | |
| CH458375A (de) | 1968-06-30 |
| SE321684B (enrdf_load_stackoverflow) | 1970-03-16 |
| DK124261B (da) | 1972-10-02 |
| LU44720A1 (enrdf_load_stackoverflow) | 1963-12-28 |
| NO115111B (enrdf_load_stackoverflow) | 1968-07-29 |
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