GB1039963A - Improvements relating to pyrazole derivatives - Google Patents
Improvements relating to pyrazole derivativesInfo
- Publication number
- GB1039963A GB1039963A GB22407/64A GB2240764A GB1039963A GB 1039963 A GB1039963 A GB 1039963A GB 22407/64 A GB22407/64 A GB 22407/64A GB 2240764 A GB2240764 A GB 2240764A GB 1039963 A GB1039963 A GB 1039963A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- pyrazole
- hydrogen atom
- alkyl
- hydroxyalkyl
- 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
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- -1 morpholino, pyrrolidino Chemical group 0.000 abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000000945 filler Substances 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002261 Corn starch Polymers 0.000 abstract 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- 229930195725 Mannitol Natural products 0.000 abstract 1
- KUYUDSWRRVHHQH-UHFFFAOYSA-N N,N-dimethyl-4-(1H-pyrazol-5-yliminomethyl)aniline Chemical compound CN(C1=CC=C(C=NC2=NNC=C2)C=C1)C KUYUDSWRRVHHQH-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 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
- 230000003110 anti-inflammatory effect Effects 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
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 239000003026 cod liver oil Substances 0.000 abstract 1
- 235000012716 cod liver oil Nutrition 0.000 abstract 1
- 239000008120 corn starch Substances 0.000 abstract 1
- 230000003111 delayed effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 239000007902 hard capsule Substances 0.000 abstract 1
- 239000000594 mannitol Substances 0.000 abstract 1
- 235000010355 mannitol Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- KSTHOIHFANCMGF-UHFFFAOYSA-N n,n-dimethylpyrazole-1-carboxamide Chemical compound CN(C)C(=O)N1C=CC=N1 KSTHOIHFANCMGF-UHFFFAOYSA-N 0.000 abstract 1
- NISODVPEMARHIK-UHFFFAOYSA-N n-(4-bromo-1h-pyrazol-5-yl)acetamide Chemical compound CC(=O)NC=1NN=CC=1Br NISODVPEMARHIK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 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
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000007901 soft capsule Substances 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07D231/14—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 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
- C07D231/38—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
- C07D231/14—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 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of formula <FORM:1039963/C2/1> wherein the ring contains two double bonds and the -CXNR1R2 group is attached to one of the ring-nitrogen atoms, X is oxygen or sulphur, R1 is a methyl group and R2 is a C1- 6 alkyl, C3- 6 alken-2-yl, C2- 6 alkoxyalkyl, C2- 6 hydroxyalkyl, dimethylamino, or C3- 7 dimethyl- or diethylaminoalkyl, wherein the alkyl moiety has 1 to 4 carbon atoms, group, or the group -NR1R2 is a morpholino, pyrrolidino, 3,4-dehydropiperidino or 3-azabicyclo[3,2,2]nonyl group, or a group <FORM:1039963/C2/2> wherein Y1 is a hydrogen atom or a methyl group, Y2 is a hydrogen atom or a methyl, ethyl, C2- 6 hydroxyalkyl or C2- 5 alkoxycarbonyl group, and Y3 is a hydrogen atom or a C1- 6 alkyl, C2- 6 hydroxyalkyl, trifluoromethyl, C2- 5 alkoxycarbonyl, C3- 7 dimethyl- or diethylaminoalkyl, wherein the alkyl moiety has 1 to 4 carbon atoms, C7- 9 aralkyl or b -pyrrolidinoethyl group, R3 is a hydrogen atom or a C1- 3 acyl group and R4 is a hydrogen, fluorine, chlorine or bromine atom or a C1- 3 alkyl or trifluoromethyl group, and their preparation by (a) reaction of a pyrazole-1-carbonyl or -thiocarbonyl chloride, or a 1-alkoxycarbonyl or 1-alkoxythiocarbonyl pyrazole, with an amine, (b) reaction of a pyrazole with an amine carbonyl or thiocarbonyl chloride or (c) reaction of a 3(5)-p-dimethylaminobenzalamino-pyrazole with 2,4-dinitrophenylhydrazone. 3(5) - p - Dimethylaminobenzalamino - 1 - dimethylcarbamyl-pyrazole is prepared by reaction of 3-aminopyrazole and benzaldehyde to form 3 - (p - dimethylaminobenzalamino) - pyrazole, and reacting this with sodium hydride and 1-dimethylcarbamyl-pyrazole. 3 - Acetamido - 4 - bromo - pyrazole is prepared by bromination. 3-Acylamino-pyrazoles are prepared by acylation.ALSO:Pharmaceutical compositions having analgesic, anti-inflammatory and central nervous system activity comprise, in combination with a carrier, a compound of formula <FORM:1039963/A5-A6/1> wherein X is oxygen or sulphur, the ring contains two double bonds and the group -CXNR1R2 is attached to one of the nitrogen atoms, R1 is a methyl group and R2 is a C1-6 alkyl, (3-6 alken-2-yl, C2-6 alkoxyalkyl, C2-6 hydroxyalkyl, dimethylamino, or dimethyl-or diethyl-aminoalkyl wherein the alkyl moiety has 1 to 4 carbon atoms and the whole group 3 to 7 carbon atoms, or the group -NR, R2 is a morpholino, pyrolidino, 3, 4-dehydropiperidino or 3 oza-binyreo-[3, 2, 2] nonyl group, or 4 group <FORM:1039963/A5-A6/2> wherein Y1 is a hydrogen atom or a methyl group Y2 is a hydrogen atom or a methyl, ethyl, C2-6 hydroxyalkyl or C2-5 alkoxycarbonyl group, and Y3 is a hydrogen atom or a C1-6 alkyl, C2-6 hydroxyalkyl, trifluoromethyl, C2-5 alkoxycarbonyl, C3-7 dimethyl-or diethyl-aminoalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, b -pyrolidinoethyl or C7-9 aralkyl group, R3 is a hydrogen atom or a C1-3 aryl group, and R4 is a hydrogen, fluorine, chlorine or bromine atom or a C1-3 alkyl or trifluoromethyl group. The compositions may be in forms suitable for oral or parenteral administration with carriers such as water, saline, aqueous sugars, alcohols, oils, including cod-liver oil, or gums, and may contain other pharmaceutically active substances, for example vitamins, analgesics, tranquillisers, antibiotics and anti tussive agents. The forms taken may be hard or soft capsules, delayed release oral forms, powders, tablets, and oral or injectable solutions or suspensions, e.g. an injectable saline solution, a tablet with gelatin, talc, and a mannitol filler, and a capsule with a corn starch filler.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US284374A US3277100A (en) | 1963-05-31 | 1963-05-31 | Novel substituted pyrazoles |
| US284323A US3274203A (en) | 1963-05-31 | 1963-05-31 | 1-carbamyl and thiocarbamyl-3-amino-4-nonsubstituted and substituted pyrazoles |
| US556540A US3362877A (en) | 1963-05-31 | 1966-06-10 | Use of 3-amino-n-carbamylpyrazoles as analgesic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1039963A true GB1039963A (en) | 1966-08-24 |
Family
ID=27403460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22407/64A Expired GB1039963A (en) | 1963-05-31 | 1964-05-29 | Improvements relating to pyrazole derivatives |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US3274203A (en) |
| CH (1) | CH454883A (en) |
| DK (1) | DK116443B (en) |
| GB (1) | GB1039963A (en) |
| SE (1) | SE301812B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694456A (en) * | 1970-05-08 | 1972-09-26 | Takeda Chemical Industries Ltd | 1-disubstituted aminopyrazoles |
| US3940484A (en) * | 1971-12-07 | 1976-02-24 | The Boots Company Limited | Insecticidal compositions and methods of combatting insects using substituted imidazoles |
| US3760083A (en) * | 1972-05-01 | 1973-09-18 | American Cyanamid Co | A method for the use of 5-amino-3-ethyl-1-(m-fluorophenyl)-4-pyrazolecarboxamide |
| US3760084A (en) * | 1972-05-01 | 1973-09-18 | American Cyanamid Co | Method of using 5-amino-1-phenyl or substituted phenyl-4-pyrazolecarbonitriles or carbox-amides |
| US3760082A (en) * | 1972-05-01 | 1973-09-18 | American Cyanamid Co | Compositions containing 5-amino-3-ethyl-1-phenyl-4-pyrazolecarboxamides and methods of using the same |
| DE2458965C3 (en) * | 1974-12-13 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | 3-Amino-indazole-N-carboxylic acid derivatives, process for their preparation and pharmaceuticals containing them |
| DE102005057894A1 (en) * | 2005-12-02 | 2007-06-06 | Basf Ag | Stabilized polymerizable mixtures |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476986A (en) * | 1949-07-26 | Elmobe louis martin | ||
| US2817666A (en) * | 1956-10-29 | 1957-12-24 | Monsanto Chemicals | N(3-methyl-5-pyrazolone)-halo-carboxanilides |
| US3080287A (en) * | 1957-08-05 | 1963-03-05 | Lewenstein Mozes Juda | Analgesic compositions |
| US3013001A (en) * | 1959-03-26 | 1961-12-12 | Union Carbide Corp | N-substituted pyrazole compounds and polymerization products thereof |
| US2998419A (en) * | 1959-10-30 | 1961-08-29 | Du Pont | Certain amino, dicyano pyrazoles and process |
| US2998425A (en) * | 1959-11-02 | 1961-08-29 | Du Pont | Certain aminopyrazole carbonitriles containing a fluoroalkyl substituent |
| US2998426A (en) * | 1959-11-02 | 1961-08-29 | Du Pont | Certain amine, cyano pyrazoles |
| US3060091A (en) * | 1961-02-13 | 1962-10-23 | Ciba Geigy Corp | Analgesic composition consisting of morphines and amino-indanes |
| US3308130A (en) * | 1962-04-26 | 1967-03-07 | Du Pont | N-disubstituted carbamyl pyrazoles |
-
1963
- 1963-05-31 US US284323A patent/US3274203A/en not_active Expired - Lifetime
- 1963-05-31 US US284374A patent/US3277100A/en not_active Expired - Lifetime
-
1964
- 1964-05-26 SE SE6369/64A patent/SE301812B/xx unknown
- 1964-05-28 CH CH696364A patent/CH454883A/en unknown
- 1964-05-29 DK DK270564AA patent/DK116443B/en unknown
- 1964-05-29 GB GB22407/64A patent/GB1039963A/en not_active Expired
-
1966
- 1966-06-10 US US556540A patent/US3362877A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE301812B (en) | 1968-06-24 |
| DK116443B (en) | 1970-01-12 |
| CH454883A (en) | 1968-04-30 |
| US3274203A (en) | 1966-09-20 |
| US3362877A (en) | 1968-01-09 |
| US3277100A (en) | 1966-10-04 |
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