IL43261A - 5-benzoyloxy-n-aminoalkyl(bicyclo(2,2,1)heptane)-(2,3)dicarboximide derivatives their preparation and anti-arrhythmic compositions containing them - Google Patents
5-benzoyloxy-n-aminoalkyl(bicyclo(2,2,1)heptane)-(2,3)dicarboximide derivatives their preparation and anti-arrhythmic compositions containing themInfo
- Publication number
- IL43261A IL43261A IL43261A IL4326173A IL43261A IL 43261 A IL43261 A IL 43261A IL 43261 A IL43261 A IL 43261A IL 4326173 A IL4326173 A IL 4326173A IL 43261 A IL43261 A IL 43261A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- alkyl
- integer
- hydrogen
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title 1
- 230000003288 anthiarrhythmic effect Effects 0.000 title 1
- 239000003416 antiarrhythmic agent Substances 0.000 title 1
- 150000008056 dicarboxyimides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 238000000034 method Methods 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 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 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 238000010992 reflux Methods 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- -1 benzoyl halide Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000004682 monohydrates Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000004684 trihydrates Chemical class 0.000 claims 3
- SDQGRJKYBWFIDP-UHFFFAOYSA-N 3-but-2-enyl-4-methyloxolane-2,5-dione Chemical compound CC=CCC1C(C)C(=O)OC1=O SDQGRJKYBWFIDP-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 238000005815 base catalysis Methods 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00290596A US3850921A (en) | 1972-09-20 | 1972-09-20 | Derivatives of 2,3-norbornanedicarboxamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43261A0 IL43261A0 (en) | 1974-01-14 |
| IL43261A true IL43261A (en) | 1976-11-30 |
Family
ID=23116712
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43261A IL43261A (en) | 1972-09-20 | 1973-09-18 | 5-benzoyloxy-n-aminoalkyl(bicyclo(2,2,1)heptane)-(2,3)dicarboximide derivatives their preparation and anti-arrhythmic compositions containing them |
| IL49658A IL49658A (en) | 1972-09-20 | 1973-09-18 | Bicyclo(2,2,1)heptane(2,3)dicarboximides and their preparation |
| IL49658A IL49658A0 (en) | 1972-09-20 | 1976-05-25 | Novel bicyclo(2,2,1)heptane(2,3)dicarboximides and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49658A IL49658A (en) | 1972-09-20 | 1973-09-18 | Bicyclo(2,2,1)heptane(2,3)dicarboximides and their preparation |
| IL49658A IL49658A0 (en) | 1972-09-20 | 1976-05-25 | Novel bicyclo(2,2,1)heptane(2,3)dicarboximides and their preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS59210067A (enEXAMPLES) |
| CS (1) | CS192505B2 (enEXAMPLES) |
| DD (2) | DD115663A5 (enEXAMPLES) |
| DK (1) | DK137236C (enEXAMPLES) |
| FI (1) | FI59089C (enEXAMPLES) |
| HU (2) | HU166755B (enEXAMPLES) |
| IE (1) | IE38264B1 (enEXAMPLES) |
| IL (3) | IL43261A (enEXAMPLES) |
| PH (1) | PH12308A (enEXAMPLES) |
| SE (1) | SE411207B (enEXAMPLES) |
| SU (1) | SU583749A3 (enEXAMPLES) |
| YU (2) | YU246673A (enEXAMPLES) |
| ZA (1) | ZA737458B (enEXAMPLES) |
-
1973
- 1973-09-18 IL IL43261A patent/IL43261A/en unknown
- 1973-09-18 SE SE7312732A patent/SE411207B/xx unknown
- 1973-09-18 YU YU02466/73A patent/YU246673A/xx unknown
- 1973-09-18 IL IL49658A patent/IL49658A/en unknown
- 1973-09-19 FI FI2918/73A patent/FI59089C/fi active
- 1973-09-19 DK DK512673A patent/DK137236C/da not_active IP Right Cessation
- 1973-09-19 PH PH7315035A patent/PH12308A/en unknown
- 1973-09-20 ZA ZA737458A patent/ZA737458B/xx unknown
- 1973-09-20 DD DD183523*A patent/DD115663A5/xx unknown
- 1973-09-20 SU SU7301962649A patent/SU583749A3/ru active
- 1973-09-20 CS CS736480A patent/CS192505B2/cs unknown
- 1973-09-20 HU HUOI163A patent/HU166755B/hu unknown
- 1973-09-20 HU HUOI183A patent/HU168424B/hu unknown
- 1973-09-20 DD DD173590A patent/DD111576A5/xx unknown
- 1973-09-20 IE IE1685/73A patent/IE38264B1/xx unknown
-
1976
- 1976-05-25 IL IL49658A patent/IL49658A0/xx unknown
-
1982
- 1982-07-29 YU YU01663/82A patent/YU166382A/xx unknown
-
1984
- 1984-05-02 JP JP59087826A patent/JPS59210067A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK137236B (da) | 1978-02-06 |
| FI59089C (fi) | 1981-06-10 |
| IL49658A0 (en) | 1976-07-30 |
| IL43261A0 (en) | 1974-01-14 |
| IE38264B1 (en) | 1978-02-01 |
| ZA737458B (en) | 1974-09-25 |
| DK137236C (da) | 1978-07-10 |
| IE38264L (en) | 1974-03-20 |
| HU168424B (enEXAMPLES) | 1976-04-28 |
| DD111576A5 (de) | 1975-02-20 |
| YU246673A (en) | 1983-01-21 |
| PH12308A (en) | 1979-01-16 |
| SU583749A3 (ru) | 1977-12-05 |
| FI59089B (fi) | 1981-02-27 |
| IL49658A (en) | 1976-11-30 |
| DD115663A5 (enEXAMPLES) | 1975-10-12 |
| CS192505B2 (en) | 1979-08-31 |
| JPS59210067A (ja) | 1984-11-28 |
| YU166382A (en) | 1988-08-31 |
| SE411207B (sv) | 1979-12-10 |
| HU166755B (enEXAMPLES) | 1975-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE14423T1 (de) | Hydroxamsaeurederivate vom typ der mannich-basen mit verbesserter biologischer verfuegbarkeit von nicht-steroiden entzuendungshemmern, verfahren zur herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzung. | |
| WO2013035833A1 (ja) | モルヒナン誘導体 | |
| PL243130A1 (en) | Process for preparing novel derivatives of 1,4-dihydropyridine | |
| SK3796A3 (en) | Process for the synthesis of azetidinones | |
| JP2023535815A (ja) | 抗血小板薬およびその使用 | |
| JP2025516719A (ja) | Ｎｌｒｐ３を阻害するためのオキソインドリニルアミド誘導体およびその使用 | |
| US2520264A (en) | Substituted 3, 1-benz-2, 3, 4, 5-tetrahydroazepines | |
| JP2509465B2 (ja) | 不飽和アミノ酸を含む医薬 | |
| AU7314098A (en) | New chromene compounds, a process for their preparation and pharmaceutical compositions containing them | |
| IE46484B1 (en) | Pyridinyl aminoalkyl ehers useful for treating cardiac arrhythmias | |
| IL43261A (en) | 5-benzoyloxy-n-aminoalkyl(bicyclo(2,2,1)heptane)-(2,3)dicarboximide derivatives their preparation and anti-arrhythmic compositions containing them | |
| EP0349902A2 (en) | Processes for the preparation of morniflumate and analogous compounds | |
| AU711148B2 (en) | Novel derivatives of swainsonine, processes for their preparation and their use as therapeutic agents | |
| KR101057304B1 (ko) | 키랄 촉매를 이용한 아스파르트산 유도체의 제조방법 | |
| JP2004511548A (ja) | Ｎ−置換された２−スルファニルイミダゾールの調製方法 | |
| US3951984A (en) | 3-Benzazocine compounds | |
| AU752505B2 (en) | New 8H-thieno-(2,3-b)pyrrolizin-8-one compounds, a process for their preparation and pharmaceutical compositions containing them | |
| VanAllan et al. | Reactions of 4‐dicyanomethylenepyrans with hindered primary amines | |
| KR810000857B1 (ko) | 비스-페니실라노일옥시-알칸류의 제법 | |
| SK47794A3 (en) | Chinolyl-dihydropyridinecarboxylic acid esters, method of their production, medicines containing these matters, method of their production and using of these compounds | |
| KR100572409B1 (ko) | 4ｒ-하이드록시-ｎ-벤질-2-피페리디논의 제조방법 | |
| AU4482699A (en) | Process for preparing trovafloxacin acid salts | |
| CN108299242A (zh) | 一种手性三氟甲基胺衍生物的制备方法 | |
| Zhang | I. Bis (arylthio) carbenes: Generation and reactions with vinyl isocyanates. II. Studies toward the total synthesis of stenine | |
| NZ745619B2 (en) | Thiazolidinone compounds and use thereof |