CA1068605A - Medicament based upon adenosine 5'-thiothers - Google Patents
Medicament based upon adenosine 5'-thiothersInfo
- Publication number
- CA1068605A CA1068605A CA254,477A CA254477A CA1068605A CA 1068605 A CA1068605 A CA 1068605A CA 254477 A CA254477 A CA 254477A CA 1068605 A CA1068605 A CA 1068605A
- Authority
- CA
- Canada
- Prior art keywords
- group
- cells
- cooh
- composition according
- sia
- 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
- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 title abstract description 7
- 239000003814 drug Substances 0.000 title description 4
- 230000009466 transformation Effects 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 230000002246 oncogenic effect Effects 0.000 claims abstract description 12
- 230000005764 inhibitory process Effects 0.000 claims abstract description 11
- 230000001621 anti-mitogenic effect Effects 0.000 claims abstract description 9
- 230000001413 cellular effect Effects 0.000 claims abstract description 6
- 238000001727 in vivo Methods 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 6
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 abstract description 4
- 201000011510 cancer Diseases 0.000 abstract description 3
- 208000036142 Viral infection Diseases 0.000 abstract description 2
- 230000009385 viral infection Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 40
- 239000003112 inhibitor Substances 0.000 description 27
- 230000000694 effects Effects 0.000 description 17
- 210000004698 lymphocyte Anatomy 0.000 description 15
- 239000003226 mitogen Substances 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 230000002297 mitogenic effect Effects 0.000 description 12
- 241000283973 Oryctolagus cuniculus Species 0.000 description 11
- 241000700605 Viruses Species 0.000 description 11
- 210000002950 fibroblast Anatomy 0.000 description 11
- 210000001161 mammalian embryo Anatomy 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- 241000287828 Gallus gallus Species 0.000 description 10
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 10
- 238000010348 incorporation Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 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 8
- 241000699670 Mus sp. Species 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- 210000000952 spleen Anatomy 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000002427 irreversible effect Effects 0.000 description 5
- 239000003550 marker Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 4
- 206010039491 Sarcoma Diseases 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002158 endotoxin Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 229920006008 lipopolysaccharide Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 4
- 229940045145 uridine Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 102000055027 Protein Methyltransferases Human genes 0.000 description 3
- 108700040121 Protein Methyltransferases Proteins 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- IYSNPOMTKFZDHZ-KQYNXXCUSA-N 5'-chloro-5'-deoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O IYSNPOMTKFZDHZ-KQYNXXCUSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010064912 Malignant transformation Diseases 0.000 description 2
- 102000016397 Methyltransferase Human genes 0.000 description 2
- 108060004795 Methyltransferase Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960001570 ademetionine Drugs 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000036212 malign transformation Effects 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920002477 rna polymer Polymers 0.000 description 2
- 239000012622 synthetic inhibitor Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- AFPVVTILDKMYJF-SOVPELCUSA-N (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-[hydroxy(sulfonyl)methyl]oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](C(O)=S(=O)=O)[C@@H](O)[C@H]1O AFPVVTILDKMYJF-SOVPELCUSA-N 0.000 description 1
- IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 108010062580 Concanavalin A Proteins 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229940079131 Methylase inhibitor Drugs 0.000 description 1
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- 108010013639 Peptidoglycan Proteins 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- ZJUKTBDSGOFHSH-WFMPWKQPSA-N S-Adenosylhomocysteine Chemical class O[C@@H]1[C@H](O)[C@@H](CSCC[C@H](N)C(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZJUKTBDSGOFHSH-WFMPWKQPSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000006607 hypermethylation Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7517972A FR2313937A1 (fr) | 1975-06-09 | 1975-06-09 | Medicament a base de 5' thioethers de l'adenosine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068605A true CA1068605A (en) | 1979-12-25 |
Family
ID=9156224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,477A Expired CA1068605A (en) | 1975-06-09 | 1976-06-09 | Medicament based upon adenosine 5'-thiothers |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS52125633A (enExample) |
| CA (1) | CA1068605A (enExample) |
| DE (1) | DE2625835A1 (enExample) |
| FR (1) | FR2313937A1 (enExample) |
| GB (1) | GB1555991A (enExample) |
| OA (1) | OA05351A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7802074A (nl) * | 1978-02-24 | 1979-08-28 | Lely Nv C Van Der | Inrichting voor het verspreiden van korrel- en/of poedervormig materiaal. |
| FR2424027A1 (fr) * | 1978-04-28 | 1979-11-23 | Merieux Inst | Nouveau medicament, notamment sedatif et inducteur de sommeil et compositions pharmaceutiques la renfermant |
| IT1193529B (it) * | 1980-04-22 | 1988-07-08 | Bioresearch Srl | Derivati adenosinici ad attivita' antinfiammatoria ed analgesica e composizioni terapeutiche che li contengono come principio attivo |
| IT1227049B (it) * | 1988-07-29 | 1991-03-14 | Bioresearch Spa | Impiego di derivati adenosinici per la preparazione di composizioni farmaceutiche aventi attivita' immunostimolante. |
| IT1229479B (it) * | 1989-03-13 | 1991-09-03 | Bioresearch Spa | Impiego di 5' deossi 5' metiltioadenosina, di s adenosilmetionina e dei loro sali per la preparazione di composizioni farmaceutiche atte a favorire la crescita dei capelli in soggetti affetti da calvizie e composizioni farmaceutiche relative. |
| CA2299271C (en) * | 1997-08-07 | 2009-02-03 | University Of Utah | Prodrugs and conjugates of thiol- and selenol- containing compounds and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH81A (de) * | 1889-01-09 | Louis Giroud | Kniehebelpresse mit Handkurbelantrieb, Zahnradübersetzung und Zugstange, hauptsächlich zur Herstellung von Bausteinen | |
| CH80A (fr) * | 1889-01-09 | Henri Sandoz | Ecrin à détente pour montres à répétition | |
| CH78A (de) * | 1889-01-18 | August Graemiger Anton | Apparat zum Färben, Waschen, Bleichen u. s. w., von Garn in aufgewickeltem Zustande | |
| CH79A (de) * | 1889-01-09 | Adam Sautter Johann | Uhrwerk für Taschenuhren mit offenem Federhaus, neuem Gangrücker-System und vereinfachter Werkbefestigung | |
| CH76A (fr) * | 1888-11-14 | 1889-01-09 | Carnal Paul E | Nouveau système de boîte de montre pouvant servir à volonté comme savonnette ou comme boîte à glace |
-
1975
- 1975-06-09 FR FR7517972A patent/FR2313937A1/fr active Granted
-
1976
- 1976-06-08 GB GB23702/76A patent/GB1555991A/en not_active Expired
- 1976-06-09 JP JP6668576A patent/JPS52125633A/ja active Pending
- 1976-06-09 OA OA55848A patent/OA05351A/xx unknown
- 1976-06-09 CA CA254,477A patent/CA1068605A/en not_active Expired
- 1976-06-09 DE DE19762625835 patent/DE2625835A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| FR2313937B1 (enExample) | 1978-10-06 |
| GB1555991A (en) | 1979-11-14 |
| JPS52125633A (en) | 1977-10-21 |
| FR2313937A1 (fr) | 1977-01-07 |
| OA05351A (fr) | 1981-02-28 |
| DE2625835A1 (de) | 1976-12-23 |
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