CH500928A - Verfahren zur Herstellung von Methoxyalkyladamantanen und deren Verwendung - Google Patents
Verfahren zur Herstellung von Methoxyalkyladamantanen und deren VerwendungInfo
- Publication number
- CH500928A CH500928A CH603968A CH603968A CH500928A CH 500928 A CH500928 A CH 500928A CH 603968 A CH603968 A CH 603968A CH 603968 A CH603968 A CH 603968A CH 500928 A CH500928 A CH 500928A
- Authority
- CH
- Switzerland
- Prior art keywords
- methoxy
- virus
- compounds
- agent
- tests
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 17
- 239000003443 antiviral agent Substances 0.000 title abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 241000700605 Viruses Species 0.000 claims abstract description 26
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims abstract description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 241000700584 Simplexvirus Species 0.000 claims abstract description 9
- 206010022000 influenza Diseases 0.000 claims abstract description 8
- 241001465754 Metazoa Species 0.000 claims abstract description 5
- 241000991587 Enterovirus C Species 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 29
- 238000012360 testing method Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- -1 1-methoxy-3,5,7-trimethyladamantane Chemical compound 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 10
- 241000699670 Mus sp. Species 0.000 claims description 9
- 230000000840 anti-viral effect Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 7
- ZYOWNFGAUMRKCG-UHFFFAOYSA-N 1-methoxy-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC2(C)CC1(OC)C3 ZYOWNFGAUMRKCG-UHFFFAOYSA-N 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910001923 silver oxide Inorganic materials 0.000 claims description 5
- JGMHRURFTNPHNY-UHFFFAOYSA-N 1-ethyl-3-methoxy-5,7-dimethyladamantane Chemical compound COC12CC3(CC(CC(C1)(C3)C)(C2)C)CC JGMHRURFTNPHNY-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002474 experimental method Methods 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- RTPQXHZLCUUIJP-UHFFFAOYSA-N 1,2-dimethyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2(C)C3 RTPQXHZLCUUIJP-UHFFFAOYSA-N 0.000 claims description 2
- 208000009889 Herpes Simplex Diseases 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 13
- 241000723873 Tobacco mosaic virus Species 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 abstract description 2
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- DUNJTZWVWZSEKK-UHFFFAOYSA-N 1-bromo-3,5,7-trimethyladamantane Chemical compound C1C(C2)(C)CC3(C)CC1(C)CC2(Br)C3 DUNJTZWVWZSEKK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006959 Williamson synthesis reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- WCACLGXPFTYVEL-UHFFFAOYSA-N 1,3,5-trimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(C)C3 WCACLGXPFTYVEL-UHFFFAOYSA-N 0.000 description 1
- DJUDQBVINJIMFO-UHFFFAOYSA-N 3-bromoadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2(Br)CC1(C(=O)O)C3 DJUDQBVINJIMFO-UHFFFAOYSA-N 0.000 description 1
- LIBKGLXSYYLLBX-UHFFFAOYSA-N 3-methoxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1(OC)CC2(C(O)=O)C3 LIBKGLXSYYLLBX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 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 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 241001495644 Nicotiana glutinosa Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 239000005723 virus inoculator Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US633385A US3383423A (en) | 1967-04-25 | 1967-04-25 | Methoxyalkyladamantanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500928A true CH500928A (de) | 1970-12-31 |
Family
ID=24539424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH603968A CH500928A (de) | 1967-04-25 | 1968-04-24 | Verfahren zur Herstellung von Methoxyalkyladamantanen und deren Verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3383423A (ref) |
| BE (1) | BE714208A (ref) |
| CH (1) | CH500928A (ref) |
| DE (1) | DE1768126A1 (ref) |
| FR (2) | FR8430M (ref) |
| GB (1) | GB1166583A (ref) |
| NL (1) | NL6805785A (ref) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6056690B2 (ja) * | 1977-04-11 | 1985-12-11 | 花王株式会社 | ３−アルコキシ−４−ホモイソツイスタンおよびその製法ならびにこれを含有する香料組成物 |
| JPS6056691B2 (ja) * | 1977-04-11 | 1985-12-11 | 花王株式会社 | １−アルコキシトリシクロ〔４．３．１．１▲↑２，↑５▼〕ウンデカンおよびその製法ならびにこれを含有する香料組成物 |
| RU2582620C2 (ru) * | 2012-07-11 | 2016-04-27 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения 1-адамантилалкиловых эфиров |
| WO2017127306A1 (en) | 2016-01-18 | 2017-07-27 | Arisan Therapeutics | Adamatane derivatives for the treatment of filovirus infection |
| US11548893B2 (en) | 2017-07-15 | 2023-01-10 | Arisan Therapeutics Inc. | Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection |
-
1967
- 1967-04-25 US US633385A patent/US3383423A/en not_active Expired - Lifetime
-
1968
- 1968-04-03 DE DE19681768126 patent/DE1768126A1/de active Pending
- 1968-04-03 GB GB05978/68A patent/GB1166583A/en not_active Expired
- 1968-04-24 FR FR149236A patent/FR8430M/fr not_active Expired
- 1968-04-24 NL NL6805785A patent/NL6805785A/xx unknown
- 1968-04-24 CH CH603968A patent/CH500928A/de not_active IP Right Cessation
- 1968-04-24 FR FR1589653D patent/FR1589653A/fr not_active Expired
- 1968-04-25 BE BE714208D patent/BE714208A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6805785A (ref) | 1968-10-28 |
| FR8430M (ref) | 1971-07-08 |
| DE1768126A1 (de) | 1971-10-07 |
| US3383423A (en) | 1968-05-14 |
| BE714208A (ref) | 1968-10-25 |
| GB1166583A (en) | 1969-10-08 |
| FR1589653A (ref) | 1970-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |