GB921943A - Anti-hypertensive compositions - Google Patents
Anti-hypertensive compositionsInfo
- Publication number
- GB921943A GB921943A GB39764/60A GB3976460A GB921943A GB 921943 A GB921943 A GB 921943A GB 39764/60 A GB39764/60 A GB 39764/60A GB 3976460 A GB3976460 A GB 3976460A GB 921943 A GB921943 A GB 921943A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- carbon atoms
- ethyl
- butylamino
- alkyl
- 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
- 230000003276 anti-hypertensive effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 150000001412 amines Chemical class 0.000 abstract 8
- -1 hydroxy amines Chemical class 0.000 abstract 7
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 4
- 125000001302 tertiary amino group Chemical group 0.000 abstract 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 3
- YXIAJHJGVGZXCG-UHFFFAOYSA-N n-tert-butyl-2-methylbut-3-yn-2-amine Chemical compound CC(C)(C)NC(C)(C)C#C YXIAJHJGVGZXCG-UHFFFAOYSA-N 0.000 abstract 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 abstract 2
- KUBBTBGPUYUKBX-UHFFFAOYSA-N 3-ethyl-3-(propan-2-ylamino)pentan-2-ol Chemical compound C(C)(C)NC(C(C)O)(CC)CC KUBBTBGPUYUKBX-UHFFFAOYSA-N 0.000 abstract 2
- 208000001953 Hypotension Diseases 0.000 abstract 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- DIWKDXFZXXCDLF-UHFFFAOYSA-N chloroethyne Chemical group ClC#C DIWKDXFZXXCDLF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical group NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 abstract 2
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 208000021822 hypotensive Diseases 0.000 abstract 2
- 230000001077 hypotensive effect Effects 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- KHFZSXVUPAIVJP-UHFFFAOYSA-N 1-(3-ethylpent-1-yn-3-yl)pyrrolidine Chemical compound CCC(CC)(C#C)N1CCCC1 KHFZSXVUPAIVJP-UHFFFAOYSA-N 0.000 abstract 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 abstract 1
- XXWIEGOAVMLISY-UHFFFAOYSA-N 3,4,4-trimethylpent-1-yn-3-ol Chemical compound CC(C)(C)C(C)(O)C#C XXWIEGOAVMLISY-UHFFFAOYSA-N 0.000 abstract 1
- OLZBOELZEIGQME-UHFFFAOYSA-N 3,4-dimethyl-N-propan-2-ylpent-1-en-3-amine Chemical compound C(C)(C)NC(C=C)(C(C)C)C OLZBOELZEIGQME-UHFFFAOYSA-N 0.000 abstract 1
- POXXEBWIHAYJMJ-UHFFFAOYSA-N 3,4-dimethylhex-1-yn-3-ol Chemical compound CCC(C)C(C)(O)C#C POXXEBWIHAYJMJ-UHFFFAOYSA-N 0.000 abstract 1
- KKNNIKDAOBTLQK-UHFFFAOYSA-N 3-(tert-butylamino)-3-ethylpentan-2-one Chemical compound C(C)(C)(C)NC(C(C)=O)(CC)CC KKNNIKDAOBTLQK-UHFFFAOYSA-N 0.000 abstract 1
- YEXSFMHTSJYBQT-UHFFFAOYSA-N 3-(tert-butylamino)-3-methylbutan-2-ol Chemical compound CC(O)C(C)(C)NC(C)(C)C YEXSFMHTSJYBQT-UHFFFAOYSA-N 0.000 abstract 1
- KAKMQXMFLDWNLR-UHFFFAOYSA-N 3-(tert-butylamino)-3-methylbutan-2-one 3-(tert-butylamino)-3-methylpentan-2-one Chemical compound C(C)(C)(C)NC(C(C)=O)(C)C.C(C)(C)(C)NC(C(C)=O)(CC)C KAKMQXMFLDWNLR-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- OEJVHSXEMITMPO-UHFFFAOYSA-N 3-chloro-3,4,4-trimethylpent-1-yne Chemical compound CC(C)(C)C(C)(Cl)C#C OEJVHSXEMITMPO-UHFFFAOYSA-N 0.000 abstract 1
- HRGLJAYJNDITLN-UHFFFAOYSA-N 3-chloro-3,4-dimethylhex-1-yne 3-chloro-4-methyl-3-propan-2-ylpent-1-yne Chemical compound ClC(C#C)(C(CC)C)C.ClC(C#C)(C(C)C)C(C)C HRGLJAYJNDITLN-UHFFFAOYSA-N 0.000 abstract 1
- FIWXOOQGZBOZRR-UHFFFAOYSA-N 3-chloro-3,4-dimethylpent-1-yne Chemical compound CC(C)C(C)(Cl)C#C FIWXOOQGZBOZRR-UHFFFAOYSA-N 0.000 abstract 1
- UPIWOJMBVNVQAN-UHFFFAOYSA-N 3-chloro-3-ethylhex-1-yne Chemical compound ClC(C#C)(CCC)CC UPIWOJMBVNVQAN-UHFFFAOYSA-N 0.000 abstract 1
- QSILYWCNPOLKPN-UHFFFAOYSA-N 3-chloro-3-methylbut-1-yne Chemical compound CC(C)(Cl)C#C QSILYWCNPOLKPN-UHFFFAOYSA-N 0.000 abstract 1
- JZQHFGKCHMNCOB-UHFFFAOYSA-N 3-chloro-3-methylhept-1-yne Chemical compound ClC(C#C)(CCCC)C JZQHFGKCHMNCOB-UHFFFAOYSA-N 0.000 abstract 1
- XSBCXCUGZNHPFQ-UHFFFAOYSA-N 3-chloro-3-methylhex-1-yne Chemical compound CCCC(C)(Cl)C#C XSBCXCUGZNHPFQ-UHFFFAOYSA-N 0.000 abstract 1
- VHVHCTHYIICZJS-UHFFFAOYSA-N 3-ethyl-n-propan-2-ylpent-1-yn-3-amine Chemical compound CCC(CC)(C#C)NC(C)C VHVHCTHYIICZJS-UHFFFAOYSA-N 0.000 abstract 1
- BKEMXUYQGYQAHP-UHFFFAOYSA-N 3-methyl-3-(2-methylbutan-2-ylamino)pentan-2-one Chemical compound C(C)(C)(CC)NC(C(C)=O)(C)CC BKEMXUYQGYQAHP-UHFFFAOYSA-N 0.000 abstract 1
- CIYHNRILEVOJGT-UHFFFAOYSA-N 3-methyl-N-propan-2-ylhex-1-yn-3-amine Chemical compound C(C)(C)NC(C#C)(CCC)C CIYHNRILEVOJGT-UHFFFAOYSA-N 0.000 abstract 1
- KHKXRZKMAVADSE-UHFFFAOYSA-N 3-methylhept-1-yn-3-ol Chemical compound CCCCC(C)(O)C#C KHKXRZKMAVADSE-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- DIFXCBNNWBBNCA-UHFFFAOYSA-N 4-methyl-3-propan-2-ylpent-1-yn-3-ol Chemical compound CC(C)C(O)(C#C)C(C)C DIFXCBNNWBBNCA-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- LYXIFDQJEFPVOQ-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.C(C)(C)NC(C=C)(CCCC)CC Chemical compound C(C1=CC=CC=C1)(=O)O.C(C)(C)NC(C=C)(CCCC)CC LYXIFDQJEFPVOQ-UHFFFAOYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000002156 adsorbate Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- ZLBFODFEYIXUJP-UHFFFAOYSA-N butanedioic acid 2-methyl-N-propan-2-ylbut-3-en-2-amine Chemical compound C(CCC(=O)O)(=O)O.C(C)(C)NC(C=C)(C)C ZLBFODFEYIXUJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 238000005538 encapsulation Methods 0.000 abstract 1
- 239000002662 enteric coated tablet Substances 0.000 abstract 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000007903 gelatin capsule Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- XFNDIVLWLWFLGD-UHFFFAOYSA-N n-ethyl-2-methylbutan-2-amine Chemical compound CCNC(C)(C)CC XFNDIVLWLWFLGD-UHFFFAOYSA-N 0.000 abstract 1
- SXGXCSASZBCDRM-UHFFFAOYSA-N n-tert-butyl-2-methylbut-3-en-2-amine Chemical compound CC(C)(C)NC(C)(C)C=C SXGXCSASZBCDRM-UHFFFAOYSA-N 0.000 abstract 1
- KZOPSPQZLMCNPF-UHFFFAOYSA-N n-tert-butyl-2-methylbutan-2-amine Chemical compound CCC(C)(C)NC(C)(C)C KZOPSPQZLMCNPF-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 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
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- QTZPHLRNSNHCGF-UHFFFAOYSA-N tert-butyl(2-methylbutan-2-yl)azanium;chloride Chemical compound [Cl-].CCC(C)(C)[NH2+]C(C)(C)C QTZPHLRNSNHCGF-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61K31/13—Amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US861167A US3067101A (en) | 1959-11-25 | 1959-11-25 | Method for controlling hypertension |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB921943A true GB921943A (en) | 1963-03-27 |
Family
ID=25335074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39764/60A Expired GB921943A (en) | 1959-11-25 | 1960-11-18 | Anti-hypertensive compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3067101A (enrdf_load_stackoverflow) |
| BE (1) | BE597453A (enrdf_load_stackoverflow) |
| FR (1) | FR786M (enrdf_load_stackoverflow) |
| GB (1) | GB921943A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999065862A1 (de) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Verfahren zur katalytischen, symmetrischen disubstitution von carbonsäureamiden mit grignard-reagenzien |
| WO1999065860A1 (de) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Verfahren zur katalytischen disubstitution von carbonsäureamiden mit wenigstens einem grignard-reagenz |
| WO1999065318A3 (de) * | 1998-06-18 | 2003-04-17 | Merck Patent Gmbh | Germinal substituierte amine |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172912A (en) * | 1965-03-09 | Haloacetylenic amines | ||
| US3242194A (en) * | 1961-04-20 | 1966-03-22 | Burroughs Wellcome Co | Thenyl guanidines |
| AT249885B (de) * | 1961-10-05 | 1966-10-10 | Farmaceutici Italia | Verfahren zur Herstellung eines neuen Hexapeptids |
| US3268546A (en) * | 1964-05-12 | 1966-08-23 | Mcneilab Inc | Certain 2-benzoxazolinone compounds having methoxy and halo substituents |
| CH426861A (de) * | 1963-06-06 | 1966-12-31 | Sandoz Ag | Verfahren zur Herstellung eines bisher unbekannten Polypeptids |
| US3494964A (en) * | 1969-01-13 | 1970-02-10 | Lilly Co Eli | Alpha-halo-alpha-amino ketones |
| US4201725A (en) * | 1974-05-20 | 1980-05-06 | Labaz | Secondary amines |
| US4048334A (en) * | 1974-05-20 | 1977-09-13 | Labaz | Active derivatives of methylamino in therapeutic compositions and methods of use |
| US4026925A (en) * | 1974-05-20 | 1977-05-31 | Labaz | Active derivatives of methylamine, therapeutic compositions containing the same and processes for preparing the said derivatives and compositions |
| US4057644A (en) * | 1975-08-22 | 1977-11-08 | Labaz | Active derivatives of methylamine in therapeutic compositions and methods of use |
| US6593340B1 (en) * | 2000-02-28 | 2003-07-15 | Cv Technologies, Inc. | Pharmaceutical compositions containing N-propargylphentermine and related analogs to treat neurodegeneration and/or depression |
| KR100939243B1 (ko) * | 2001-01-19 | 2010-01-29 | 인스티튜트 오브 파마콜로지 앤드 톡시콜로지 아캐더미 오브 밀리터리 메디칼 사이언시스 피.엘.에이. 차이나 | 포타슘 채널의 기능을 조절하는 아민 유도체, 그의제조방법 및 용도 |
| CN117296846A (zh) * | 2023-09-27 | 2023-12-29 | 山东农业大学 | 一种引诱剂组合物及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613208A (en) * | 1949-06-29 | 1952-10-07 | Rohm & Haas | Tertiary aminomethylbenzenes |
-
1959
- 1959-11-25 US US861167A patent/US3067101A/en not_active Expired - Lifetime
-
1960
- 1960-11-18 GB GB39764/60A patent/GB921943A/en not_active Expired
- 1960-11-24 BE BE597453A patent/BE597453A/fr unknown
- 1960-11-24 FR FR844941A patent/FR786M/fr active Active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999065862A1 (de) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Verfahren zur katalytischen, symmetrischen disubstitution von carbonsäureamiden mit grignard-reagenzien |
| WO1999065860A1 (de) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Verfahren zur katalytischen disubstitution von carbonsäureamiden mit wenigstens einem grignard-reagenz |
| US6448445B1 (en) | 1998-06-18 | 2002-09-10 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Method for catalytically disubstituting carboxylic acid amides with at least one grignard reagent |
| US6515180B1 (en) | 1998-06-18 | 2003-02-04 | Merck Patent Gesellschaft | Method for the catalytic, symmetric disubstitution of carboxylic acid amides with grignard reagents |
| WO1999065318A3 (de) * | 1998-06-18 | 2003-04-17 | Merck Patent Gmbh | Germinal substituierte amine |
| WO1999065864A3 (de) * | 1998-06-18 | 2003-05-22 | Merck Patent Gmbh | Geminal substituierte amine |
| WO1999065855A3 (de) * | 1998-06-18 | 2003-12-11 | Merck Patent Gmbh | Kombinatorische bibliotheken geminal substituierter amine |
Also Published As
| Publication number | Publication date |
|---|---|
| US3067101A (en) | 1962-12-04 |
| BE597453A (fr) | 1961-05-24 |
| FR786M (enrdf_load_stackoverflow) | 1961-09-04 |
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