ES302369A1 - Method of preparation of triciclic compounds. (Machine-translation by Google Translate, not legally binding) - Google Patents
Method of preparation of triciclic compounds. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES302369A1 ES302369A1 ES0302369A ES302369A ES302369A1 ES 302369 A1 ES302369 A1 ES 302369A1 ES 0302369 A ES0302369 A ES 0302369A ES 302369 A ES302369 A ES 302369A ES 302369 A1 ES302369 A1 ES 302369A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- reaction
- alkyl
- see formula
- mono
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 150000001412 amines Chemical class 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 alkyl ketone oximes Chemical class 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 238000006434 Ritter amidation reaction Methods 0.000 abstract 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000003944 halohydrins Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
- C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Method of preparation of tricyclic compounds of the following formula ** (See formula) ** where Z is a link (see formula) direct; A is (see formula) and B is H; or Z is CH2-; A is H and B is (see formula) and in which the substitutes R, X and Y of the previous formula are: X and Y can be the same or different and are hydrogen, methyl or ethyl; and R is -N (CH2) n, where n is 2, 3, 4, 5 or 6 -NR 1 R 2; O -N=CHR3, where R1 is hydrogen: alkyl of 1 to 6 carbon atoms; mono-substituted alkyl of 1 to 6 carbon atoms, where the substitute is hydroxyl, alkoxy of 1 to 2 carbon atoms, -NH2, -NHR4 or -NR4R5, where R4 and R5 may be the same or different and each of them is an alkyl radical of 1 to 4 carbon atoms; alkenyl of 2 to 6 carbon atoms; alkynyl of 2 to 6 carbon atoms; cyclopropyl; cyclobutyl; cyclopropylmethyl; cyclobutylmethyl; R2 is R1; chlorine; bromine; formyl; -CH2COOH; -CH2COOCH3 or -CH2COOCH5, provided that when R1 is alkenyl or alkynyl having the unsaturated bond in the 1-position, R2 is alkyl or mono-substituted alkyl, as defined above; Y R3 is aliphatic; mono-substituted aliphatic, where the substitute is aromatic or heterocyclic; aromatic; or heterocyclic containing no more than 12 carbon atoms, which method comprises the reduction of the corresponding carboxylic acid amides, or the reduction of the corresponding alkyl ketone oximes, or the reaction of the corresponding substituted methanols according to the Ritter reaction with subsequent hydrolysis, or by reaction of a corresponding amine with ethylenic oxide, or by alkylation of the corresponding amines with suitable aminoalkyl halides, or by reaction of the corresponding amines with ethylenic halohydrins, or by reaction of the corresponding amines with aldehydes. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29723363A | 1963-07-24 | 1963-07-24 | |
| US376259A US3352912A (en) | 1963-07-24 | 1964-06-18 | Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES302369A1 true ES302369A1 (en) | 1965-03-16 |
Family
ID=26970055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0302369A Expired ES302369A1 (en) | 1963-07-24 | 1964-07-23 | Method of preparation of triciclic compounds. (Machine-translation by Google Translate, not legally binding) |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3352912A (en) |
| AT (1) | AT279581B (en) |
| BE (1) | BE650919A (en) |
| BR (1) | BR6460975D0 (en) |
| CH (2) | CH476673A (en) |
| DE (3) | DE1793207A1 (en) |
| DK (3) | DK112027B (en) |
| ES (1) | ES302369A1 (en) |
| FI (3) | FI42322B (en) |
| FR (1) | FR1572956A (en) |
| GB (1) | GB1069563A (en) |
| IL (1) | IL21753A (en) |
| NL (2) | NL6408505A (en) |
| SE (3) | SE320363B (en) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449422A (en) * | 1966-02-09 | 1969-06-10 | Smithkline Corp | Pentacycloundecane amines |
| DE1294371B (en) * | 1966-12-21 | 1969-05-08 | Penicillin Ges Dauelsberg & Co | Process for the preparation of 1-aminoadamantane and its N-alkyl or N-cyclohexyl derivatives |
| US3489802A (en) * | 1967-01-23 | 1970-01-13 | Du Pont | Preparation of alpha-methyl-1-adamantane-methylamine and alpha,4 - dimethyl - 1 - bicyclo(2,2,2)octane methylamine |
| NL6900004A (en) * | 1969-01-02 | 1970-07-06 | ||
| US3682922A (en) * | 1969-01-16 | 1972-08-08 | Searle & Co | N-acyl-n-{8 (n{40 ,n{40 -disubstituted amino)-alkyl{9 -1-adamantylmethylamines |
| JPS4828903B1 (en) * | 1969-07-19 | 1973-09-05 | ||
| US3624086A (en) * | 1969-11-10 | 1971-11-30 | Searle & Co | Adamantanecarboxamidoalkanoic acid amides |
| US3852339A (en) * | 1970-06-15 | 1974-12-03 | Squibb & Sons Inc | Aminoalkoxyphenylurea derivatives |
| US3879400A (en) * | 1973-11-16 | 1975-04-22 | Upjohn Co | 1-Lower alkyl-(1-adamantylmethyl)piperidines and process for their preparation |
| JPS5346950A (en) * | 1976-10-12 | 1978-04-27 | Kao Corp | (54)1-acetylaminotricyclo(4,3,1,12,5)undecane and its preparation |
| US4351847A (en) * | 1981-06-26 | 1982-09-28 | Pennwalt Corporation | Antiviral alpha, alpha-dialkyl adamantylethylamines |
| US4551552A (en) * | 1984-05-23 | 1985-11-05 | E. I. Du Pont De Nemours And Company | Process for preparing rimantadine |
| US4751245A (en) * | 1986-06-25 | 1988-06-14 | E. R. Squibb & Sons, Inc. | Antifungal derivatives of N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine and method of using same |
| US5576355A (en) * | 1993-06-04 | 1996-11-19 | Mobil Oil Corp. | Diamondoid derivatives for pharmaceutical use |
| US5684024A (en) * | 1996-01-25 | 1997-11-04 | Viropharma Incorporated | Pyrazole dimers compositions and methods for treating influenza |
| US5821243A (en) * | 1996-07-22 | 1998-10-13 | Viropharma Incorporated | Compounds compositions and methods for treating influenza |
| PT870757E (en) * | 1997-04-10 | 2002-09-30 | Pfizer | ADAMANTAN DERIVATIVES SUBSTITUTED BY FLUORO |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| WO2003004461A1 (en) * | 2001-07-02 | 2003-01-16 | Schering Corporation | Drugs for treating viral infections |
| SE0103836D0 (en) * | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| CN1649614A (en) | 2002-02-22 | 2005-08-03 | 新河药品股份有限公司 | Active agent delivery systems and methods for protecting and administering active agents |
| WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| SE0300480D0 (en) | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| GB0312609D0 (en) | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| JP5368789B2 (en) * | 2005-06-17 | 2013-12-18 | アポジー・バイオテクノロジー・コーポレイション | Sphingosine kinase inhibitor |
| AR057623A1 (en) | 2005-11-28 | 2007-12-05 | Omega Bio Pharma H K Ltd | MATERIALS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS |
| PE20091225A1 (en) | 2007-03-22 | 2009-09-16 | Astrazeneca Ab | QUINOLINE DERIVATIVES AS ANTAGONISTS OF THE P2X7 RECEPTOR |
| PE20091036A1 (en) | 2007-11-30 | 2009-08-15 | Astrazeneca Ab | QUINOLINE DERIVATIVE AS ANTAGONIST OF THE P2X7 RECEPTOR |
| WO2014068265A1 (en) | 2012-10-29 | 2014-05-08 | Cipla Limited | Antiviral phosphonate analogues and process for preparation thereof |
| EA031458B1 (en) * | 2013-12-09 | 2019-01-31 | Юнилевер Н.В. | Process of making adamantanamides |
| WO2017093354A1 (en) | 2015-11-30 | 2017-06-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Nmdar antagonists for the treatment of diseases associated with angiogenesis |
| US11548893B2 (en) | 2017-07-15 | 2023-01-10 | Arisan Therapeutics Inc. | Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection |
-
1964
- 1964-06-18 US US376259A patent/US3352912A/en not_active Expired - Lifetime
- 1964-07-18 DE DE19641793207 patent/DE1793207A1/en active Pending
- 1964-07-18 DE DE19641792295 patent/DE1792295B1/en not_active Withdrawn
- 1964-07-18 DE DE19641793208 patent/DE1793208A1/en active Pending
- 1964-07-20 BR BR160975/64A patent/BR6460975D0/en unknown
- 1964-07-20 CH CH946964A patent/CH476673A/en not_active IP Right Cessation
- 1964-07-20 CH CH1457468A patent/CH479535A/en not_active IP Right Cessation
- 1964-07-23 DK DK367964AA patent/DK112027B/en unknown
- 1964-07-23 SE SE9752/67A patent/SE320363B/xx unknown
- 1964-07-23 IL IL21753A patent/IL21753A/en unknown
- 1964-07-23 SE SE09751/67A patent/SE330693B/xx unknown
- 1964-07-23 BE BE650919D patent/BE650919A/xx unknown
- 1964-07-23 ES ES0302369A patent/ES302369A1/en not_active Expired
- 1964-07-23 SE SE8987/64A patent/SE321924B/xx unknown
- 1964-07-23 FI FI1584/64A patent/FI42322B/fi active
- 1964-07-24 NL NL6408505A patent/NL6408505A/xx unknown
- 1964-07-24 FR FR1572956D patent/FR1572956A/fr not_active Expired
- 1964-08-04 GB GB30940/64A patent/GB1069563A/en not_active Expired
- 1964-08-07 AT AT06819/68A patent/AT279581B/en not_active IP Right Cessation
-
1965
- 1965-07-09 DK DK353365AA patent/DK114199B/en unknown
- 1965-07-09 DK DK353265AA patent/DK114769B/en unknown
-
1969
- 1969-01-22 FI FI0198/69A patent/FI42211B/fi active
- 1969-01-22 FI FI0197/69A patent/FI42548B/fi active
-
1971
- 1971-02-17 NL NL7102097A patent/NL7102097A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK114769B (en) | 1969-08-04 |
| BR6460975D0 (en) | 1973-08-09 |
| FI42211B (en) | 1970-03-02 |
| DK114199B (en) | 1969-06-09 |
| SE321924B (en) | 1970-03-23 |
| DK112027B (en) | 1968-11-04 |
| IL21753A (en) | 1968-01-25 |
| BE650919A (en) | 1964-11-16 |
| SE330693B (en) | 1970-11-30 |
| AT279581B (en) | 1970-03-10 |
| DE1793208A1 (en) | 1972-04-06 |
| FR1572956A (en) | 1969-07-04 |
| DE1468769B1 (en) | 1972-06-29 |
| CH479535A (en) | 1969-10-15 |
| FI42322B (en) | 1970-03-31 |
| NL6408505A (en) | 1965-01-25 |
| DE1792295B1 (en) | 1971-05-27 |
| SE320363B (en) | 1970-02-09 |
| DE1793207A1 (en) | 1972-03-30 |
| US3352912A (en) | 1967-11-14 |
| FI42548B (en) | 1970-06-01 |
| GB1069563A (en) | 1967-05-17 |
| NL7102097A (en) | 1971-05-25 |
| CH476673A (en) | 1969-08-15 |
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