FR2522327A1 - Nouveau sel de la tromantadine, son procede de preparation et son application en therapeutique - Google Patents
Nouveau sel de la tromantadine, son procede de preparation et son application en therapeutique Download PDFInfo
- Publication number
- FR2522327A1 FR2522327A1 FR8217996A FR8217996A FR2522327A1 FR 2522327 A1 FR2522327 A1 FR 2522327A1 FR 8217996 A FR8217996 A FR 8217996A FR 8217996 A FR8217996 A FR 8217996A FR 2522327 A1 FR2522327 A1 FR 2522327A1
- Authority
- FR
- France
- Prior art keywords
- herpes
- tromantadine
- salt
- preparation
- adamantane
- 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.)
- Granted
Links
- UXQDWARBDDDTKG-UHFFFAOYSA-N tromantadine Chemical class C1C(C2)CC3CC2CC1(NC(=O)COCCN(C)C)C3 UXQDWARBDDDTKG-UHFFFAOYSA-N 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims abstract description 12
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 ACETYL-AMINO-ADAMANTANE Chemical compound 0.000 claims abstract description 4
- 208000001688 Herpes Genitalis Diseases 0.000 claims abstract description 3
- 208000004898 Herpes Labialis Diseases 0.000 claims abstract description 3
- 206010067152 Oral herpes Diseases 0.000 claims abstract description 3
- 201000004946 genital herpes Diseases 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229960000832 tromantadine Drugs 0.000 claims description 9
- 230000000840 anti-viral effect Effects 0.000 claims description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 206010019973 Herpes virus infection Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- 241000700605 Viruses Species 0.000 description 9
- 229960005486 vaccine Drugs 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000003292 kidney cell Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 108010041986 DNA Vaccines Proteins 0.000 description 1
- 229940021995 DNA vaccine Drugs 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000019552 anatomical structure morphogenesis Effects 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 210000001840 diploid cell Anatomy 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Virology (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19901/82A IT1150209B (it) | 1982-03-01 | 1982-03-01 | Composto ad attivita'antivirale, procedimento per la sua preparazione e relative composizioni farmaceutiche |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2522327A1 true FR2522327A1 (fr) | 1983-09-02 |
| FR2522327B1 FR2522327B1 (it) | 1984-12-21 |
Family
ID=11162187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8217996A Granted FR2522327A1 (fr) | 1982-03-01 | 1982-10-27 | Nouveau sel de la tromantadine, son procede de preparation et son application en therapeutique |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS58164560A (it) |
| BE (1) | BE894802A (it) |
| CH (1) | CH653990A5 (it) |
| DE (1) | DE3245188C2 (it) |
| ES (1) | ES8308533A1 (it) |
| FR (1) | FR2522327A1 (it) |
| GB (1) | GB2115816A (it) |
| GR (1) | GR77687B (it) |
| IN (1) | IN155559B (it) |
| IT (1) | IT1150209B (it) |
| LU (1) | LU84443A1 (it) |
| NL (1) | NL8204175A (it) |
| PT (1) | PT75751B (it) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2126442A1 (it) * | 1971-02-25 | 1972-10-06 | Abbott Lab | |
| US4052439A (en) * | 1976-04-30 | 1977-10-04 | Abbott Laboratories | Carboxylic esters of phosphonoacetic acid |
-
1982
- 1982-03-01 IT IT19901/82A patent/IT1150209B/it active
- 1982-10-25 JP JP57188069A patent/JPS58164560A/ja active Pending
- 1982-10-25 GR GR69622A patent/GR77687B/el unknown
- 1982-10-26 ES ES516854A patent/ES8308533A1/es not_active Expired
- 1982-10-26 BE BE2/59880A patent/BE894802A/nl not_active IP Right Cessation
- 1982-10-27 FR FR8217996A patent/FR2522327A1/fr active Granted
- 1982-10-27 PT PT75751A patent/PT75751B/pt unknown
- 1982-10-27 CH CH6269/82A patent/CH653990A5/it not_active IP Right Cessation
- 1982-10-27 LU LU84443A patent/LU84443A1/fr unknown
- 1982-10-28 GB GB08230888A patent/GB2115816A/en not_active Withdrawn
- 1982-10-28 NL NL8204175A patent/NL8204175A/nl not_active Application Discontinuation
- 1982-10-29 IN IN1276/CAL/82A patent/IN155559B/en unknown
- 1982-12-07 DE DE3245188A patent/DE3245188C2/de not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2126442A1 (it) * | 1971-02-25 | 1972-10-06 | Abbott Lab | |
| US4052439A (en) * | 1976-04-30 | 1977-10-04 | Abbott Laboratories | Carboxylic esters of phosphonoacetic acid |
Non-Patent Citations (1)
| Title |
|---|
| ARZNEIMITTEL-FORSCHUNG, vol. 23, no. 5, mai 1973 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1150209B (it) | 1986-12-10 |
| BE894802A (nl) | 1983-02-14 |
| LU84443A1 (fr) | 1983-06-13 |
| ES516854A0 (es) | 1983-09-16 |
| PT75751B (en) | 1986-03-11 |
| IT8219901A0 (it) | 1982-03-01 |
| DE3245188A1 (de) | 1983-09-15 |
| GB2115816A (en) | 1983-09-14 |
| IN155559B (it) | 1985-02-16 |
| CH653990A5 (it) | 1986-01-31 |
| NL8204175A (nl) | 1983-10-03 |
| ES8308533A1 (es) | 1983-09-16 |
| PT75751A (en) | 1982-11-01 |
| FR2522327B1 (it) | 1984-12-21 |
| JPS58164560A (ja) | 1983-09-29 |
| DE3245188C2 (de) | 1984-09-13 |
| GR77687B (it) | 1984-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |