CA1172265A - Nonaprenylamine derivatives - Google Patents
Nonaprenylamine derivativesInfo
- Publication number
- CA1172265A CA1172265A CA000376123A CA376123A CA1172265A CA 1172265 A CA1172265 A CA 1172265A CA 000376123 A CA000376123 A CA 000376123A CA 376123 A CA376123 A CA 376123A CA 1172265 A CA1172265 A CA 1172265A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- process according
- acid addition
- pharmaceutically acceptable
- acceptable acid
- 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
- 239000002253 acid Substances 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- -1 secondary amino compound Chemical class 0.000 claims abstract description 27
- AFPLNGZPBSKHHQ-UHFFFAOYSA-N Betulaprenol 9 Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO AFPLNGZPBSKHHQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 4
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 229960001989 prenylamine Drugs 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 17
- 230000000875 corresponding effect Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
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- 239000012279 sodium borohydride Substances 0.000 claims description 2
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- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 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 claims 4
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 241001515965 unidentified phage Species 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 208000005925 vesicular stomatitis Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5510780A JPS56150047A (en) | 1980-04-23 | 1980-04-23 | Nonaprenylamine derivative |
| JP55107/1980 | 1980-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1172265A true CA1172265A (en) | 1984-08-07 |
Family
ID=12989522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000376123A Expired CA1172265A (en) | 1980-04-23 | 1981-04-23 | Nonaprenylamine derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4322555A (enExample) |
| JP (1) | JPS56150047A (enExample) |
| CA (1) | CA1172265A (enExample) |
| DE (1) | DE3116232A1 (enExample) |
| FR (1) | FR2484407A1 (enExample) |
| GB (1) | GB2074165B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380668A (en) * | 1980-11-19 | 1983-04-19 | Nisshin Flour Milling Co., Ltd. | Decaprenylamine derivatives |
| JPS57192339A (en) * | 1981-05-18 | 1982-11-26 | Nisshin Flour Milling Co Ltd | Isoprenylamine derivative |
| JPS57192342A (en) * | 1981-05-18 | 1982-11-26 | Nisshin Flour Milling Co Ltd | Isoprenylamine derivative |
| DE69617918T2 (de) * | 1995-02-08 | 2002-05-16 | Nisshin Seifun Group Inc., Tokio/Tokyo | Vorbeugendes/heilendes mittel für lebererkrankungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL278610A (enExample) * | 1961-05-24 | Hoffmann La Roche | ||
| CA1147752A (en) * | 1979-05-04 | 1983-06-07 | Yoshiyuki Tahara | Isoprenylamines |
-
1980
- 1980-04-23 JP JP5510780A patent/JPS56150047A/ja active Granted
-
1981
- 1981-04-22 US US06/256,577 patent/US4322555A/en not_active Expired - Lifetime
- 1981-04-23 GB GB8112602A patent/GB2074165B/en not_active Expired
- 1981-04-23 DE DE19813116232 patent/DE3116232A1/de active Granted
- 1981-04-23 CA CA000376123A patent/CA1172265A/en not_active Expired
- 1981-04-23 FR FR8108136A patent/FR2484407A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3116232A1 (de) | 1982-03-04 |
| JPS56150047A (en) | 1981-11-20 |
| FR2484407A1 (fr) | 1981-12-18 |
| GB2074165B (en) | 1984-04-04 |
| US4322555A (en) | 1982-03-30 |
| FR2484407B1 (enExample) | 1984-12-14 |
| GB2074165A (en) | 1981-10-28 |
| JPS6253502B2 (enExample) | 1987-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |