FI59089C - Foerfarande foer framstaellning av 5-endobensoyloxi-n-(amino-(laegre)alkyl)bicyklo(2,2,1)heptan-2,3-di-endokarboxylsyraimider motverkande oregelbunden hjaertverksamhet - Google Patents
Foerfarande foer framstaellning av 5-endobensoyloxi-n-(amino-(laegre)alkyl)bicyklo(2,2,1)heptan-2,3-di-endokarboxylsyraimider motverkande oregelbunden hjaertverksamhet Download PDFInfo
- Publication number
- FI59089C FI59089C FI2918/73A FI291873A FI59089C FI 59089 C FI59089 C FI 59089C FI 2918/73 A FI2918/73 A FI 2918/73A FI 291873 A FI291873 A FI 291873A FI 59089 C FI59089 C FI 59089C
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- Finland
- Prior art keywords
- endo
- bicyclo
- formula
- compound
- heptane
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- 238000000034 method Methods 0.000 title claims description 23
- -1 benzoyl halide Chemical class 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 61
- 238000002360 preparation method Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 11
- 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 description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims 2
- 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 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
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- 230000006793 arrhythmia Effects 0.000 description 5
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- 239000012259 ether extract Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000011173 large scale experimental method Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- ZNSWGHZWUUFFKV-UHFFFAOYSA-N piperidine;pyridine Chemical compound C1CCNCC1.C1=CC=NC=C1 ZNSWGHZWUUFFKV-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000000069 prophylactic 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
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000011172 small scale experimental method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 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)
- 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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI800420A FI60199C (fi) | 1972-09-20 | 1980-02-12 | Vid framstaellning av terapeutiskt vaerdefulla 5-endo-bensoyloxi-n-(amino-(laegre)alkyl)bicyklo(2.2.1)heptan-2,3-di-endo-karboxylsyraimider som mellanprodukter anvaendbara 5-endo-hydroxi-n-(amino-(laegre)alkyl)bisyklo(2.2.1)heptan-2,3-di-endo-karboxylsyraimider och foerfarande foer deras framstaellning |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00290596A US3850921A (en) | 1972-09-20 | 1972-09-20 | Derivatives of 2,3-norbornanedicarboxamide |
| US29059672 | 1972-09-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59089B FI59089B (fi) | 1981-02-27 |
| FI59089C true FI59089C (fi) | 1981-06-10 |
Family
ID=23116712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2918/73A FI59089C (fi) | 1972-09-20 | 1973-09-19 | Foerfarande foer framstaellning av 5-endobensoyloxi-n-(amino-(laegre)alkyl)bicyklo(2,2,1)heptan-2,3-di-endokarboxylsyraimider motverkande oregelbunden hjaertverksamhet |
Country Status (13)
-
1973
- 1973-09-18 IL IL49658A patent/IL49658A/en unknown
- 1973-09-18 YU YU02466/73A patent/YU246673A/xx unknown
- 1973-09-18 IL IL43261A patent/IL43261A/en unknown
- 1973-09-18 SE SE7312732A patent/SE411207B/xx unknown
- 1973-09-19 FI FI2918/73A patent/FI59089C/fi active
- 1973-09-19 PH PH7315035A patent/PH12308A/en unknown
- 1973-09-19 DK DK512673A patent/DK137236C/da not_active IP Right Cessation
- 1973-09-20 DD DD183523*A patent/DD115663A5/xx unknown
- 1973-09-20 SU SU7301962649A patent/SU583749A3/ru active
- 1973-09-20 IE IE1685/73A patent/IE38264B1/xx unknown
- 1973-09-20 CS CS736480A patent/CS192505B2/cs unknown
- 1973-09-20 HU HUOI183A patent/HU168424B/hu unknown
- 1973-09-20 DD DD173590A patent/DD111576A5/xx unknown
- 1973-09-20 HU HUOI163A patent/HU166755B/hu unknown
- 1973-09-20 ZA ZA737458A patent/ZA737458B/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 |
|---|---|
| HU168424B (enrdf_load_stackoverflow) | 1976-04-28 |
| HU166755B (enrdf_load_stackoverflow) | 1975-05-28 |
| DK137236B (da) | 1978-02-06 |
| JPS59210067A (ja) | 1984-11-28 |
| DK137236C (da) | 1978-07-10 |
| IE38264L (en) | 1974-03-20 |
| PH12308A (en) | 1979-01-16 |
| IL49658A (en) | 1976-11-30 |
| FI59089B (fi) | 1981-02-27 |
| SU583749A3 (ru) | 1977-12-05 |
| SE411207B (sv) | 1979-12-10 |
| YU246673A (en) | 1983-01-21 |
| YU166382A (en) | 1988-08-31 |
| IL43261A0 (en) | 1974-01-14 |
| ZA737458B (en) | 1974-09-25 |
| DD115663A5 (enrdf_load_stackoverflow) | 1975-10-12 |
| IE38264B1 (en) | 1978-02-01 |
| CS192505B2 (en) | 1979-08-31 |
| IL43261A (en) | 1976-11-30 |
| IL49658A0 (en) | 1976-07-30 |
| DD111576A5 (de) | 1975-02-20 |
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