CA1039281A - 2,3,4,5-tetrahydro-4-phenyl-1h-1,4-benzodiazepine-1-carboximidamide and related compounds - Google Patents
2,3,4,5-tetrahydro-4-phenyl-1h-1,4-benzodiazepine-1-carboximidamide and related compoundsInfo
- Publication number
- CA1039281A CA1039281A CA000218682A CA218682A CA1039281A CA 1039281 A CA1039281 A CA 1039281A CA 000218682 A CA000218682 A CA 000218682A CA 218682 A CA218682 A CA 218682A CA 1039281 A CA1039281 A CA 1039281A
- Authority
- CA
- Canada
- Prior art keywords
- benzodiazepine
- phenyl
- tetrahydro
- carboximidamide
- formula
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- YGZDFCLVLCBQOZ-UHFFFAOYSA-N 4-phenyl-3,5-dihydro-2h-1,4-benzodiazepine-1-carboximidamide Chemical compound C1C2=CC=CC=C2N(C(=N)N)CCN1C1=CC=CC=C1 YGZDFCLVLCBQOZ-UHFFFAOYSA-N 0.000 title claims description 4
- 150000003839 salts Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 11
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 abstract description 3
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- -1 Eor example Chemical group 0.000 description 24
- 238000007792 addition Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NVIIQDDQTMTTMZ-UHFFFAOYSA-N diazepine-1-carboximidamide Chemical compound NC(=N)N1C=CC=CC=N1 NVIIQDDQTMTTMZ-UHFFFAOYSA-N 0.000 description 5
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FITIKXFHYYHYIP-UHFFFAOYSA-N 1,4-benzodiazepine-1-carboximidamide Chemical compound N1(C=CN=CC2=C1C=CC=C2)C(N)=N FITIKXFHYYHYIP-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- KTUNMKNQPZBWGZ-UHFFFAOYSA-N 1H-1,2-benzodiazepine-3-carboximidamide Chemical class N1N=C(C=CC2=C1C=CC=C2)C(=N)N KTUNMKNQPZBWGZ-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical class CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- FLKCNYHPOQMAOG-UHFFFAOYSA-N 4-(4-chlorophenyl)-9-methyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound CC1=CC=CC=2C(N(CC(NC21)=O)C2=CC=C(C=C2)Cl)=O FLKCNYHPOQMAOG-UHFFFAOYSA-N 0.000 description 1
- LSKKOPDCLBISFB-UHFFFAOYSA-N 4-(4-ethoxyphenyl)-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound C(C)OC1=CC=C(C=C1)N1CC(NC2=C(C1=O)C=CC=C2)=O LSKKOPDCLBISFB-UHFFFAOYSA-N 0.000 description 1
- ILPHETHYEYLQPL-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound FC(C1=CC=C(C=C1)N1CC(NC2=C(C1=O)C=CC=C2)=O)(F)F ILPHETHYEYLQPL-UHFFFAOYSA-N 0.000 description 1
- YNWPBNWQAJYCKF-UHFFFAOYSA-N 4-phenyl-1,2,3,5-tetrahydro-1,4-benzodiazepine Chemical compound C1(=CC=CC=C1)N1CCNC2=C(C1)C=CC=C2 YNWPBNWQAJYCKF-UHFFFAOYSA-N 0.000 description 1
- OUUMEHCZPBHNBK-UHFFFAOYSA-N 4-phenyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound O=C1C2=CC=CC=C2NC(=O)CN1C1=CC=CC=C1 OUUMEHCZPBHNBK-UHFFFAOYSA-N 0.000 description 1
- OJDDBYPJEBIVSV-UHFFFAOYSA-N 6-chloro-4-(4-methylphenyl)-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound ClC1=CC=CC2=C1C(N(CC(N2)=O)C2=CC=C(C=C2)C)=O OJDDBYPJEBIVSV-UHFFFAOYSA-N 0.000 description 1
- DGTDDEVAYWMXBD-UHFFFAOYSA-N 6-tert-butyl-4-phenyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound C(C)(C)(C)C1=CC=CC2=C1C(N(CC(N2)=O)C2=CC=CC=C2)=O DGTDDEVAYWMXBD-UHFFFAOYSA-N 0.000 description 1
- DQIKZSFFUMCNTF-UHFFFAOYSA-N 7-bromo-4-phenyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound BrC=1C=CC2=C(C(N(CC(N2)=O)C2=CC=CC=C2)=O)C=1 DQIKZSFFUMCNTF-UHFFFAOYSA-N 0.000 description 1
- PQKBOAVQIICBQN-UHFFFAOYSA-N 7-chloro-4-(4-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2NC(=O)C1 PQKBOAVQIICBQN-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- XKPOGTAKRKVYLS-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)N1CCN(C2=C(C1)C=CC=C2)C(N)=N Chemical compound Cl.C1(=CC=CC=C1)N1CCN(C2=C(C1)C=CC=C2)C(N)=N XKPOGTAKRKVYLS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US469172A US3869447A (en) | 1974-05-13 | 1974-05-13 | 2,3,4,5-Tetrahydro-4-phenyl-1H-1,4-benzodiazepine-1-carboximidamide and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039281A true CA1039281A (en) | 1978-09-26 |
Family
ID=23862727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000218682A Expired CA1039281A (en) | 1974-05-13 | 1975-01-27 | 2,3,4,5-tetrahydro-4-phenyl-1h-1,4-benzodiazepine-1-carboximidamide and related compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3869447A (Direct) |
| JP (1) | JPS50149693A (Direct) |
| CA (1) | CA1039281A (Direct) |
| DE (1) | DE2503450A1 (Direct) |
| FR (1) | FR2270883B1 (Direct) |
| GB (1) | GB1440742A (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087850A1 (en) * | 1982-01-04 | 1983-09-07 | The Upjohn Company | Benzodiazepines for anti-hypertensive use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481921A (en) * | 1965-10-22 | 1969-12-02 | Hoffmann La Roche | Benzodiazepines |
| US3812103A (en) * | 1967-04-11 | 1974-05-21 | Hoffmann La Roche | 2,3-dihydro-1,4-benzodiazepines |
-
1974
- 1974-05-13 US US469172A patent/US3869447A/en not_active Expired - Lifetime
-
1975
- 1975-01-27 CA CA000218682A patent/CA1039281A/en not_active Expired
- 1975-01-28 DE DE19752503450 patent/DE2503450A1/de active Pending
- 1975-01-30 GB GB411575A patent/GB1440742A/en not_active Expired
- 1975-02-01 JP JP50013941A patent/JPS50149693A/ja active Pending
- 1975-02-04 FR FR7503450A patent/FR2270883B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1440742A (en) | 1976-06-23 |
| FR2270883B1 (Direct) | 1978-07-21 |
| FR2270883A1 (Direct) | 1975-12-12 |
| US3869447A (en) | 1975-03-04 |
| DE2503450A1 (de) | 1975-11-27 |
| JPS50149693A (Direct) | 1975-11-29 |
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