CA1068605A - Medicament a base d'adenosine 5'-thioethers - Google Patents

Medicament a base d'adenosine 5'-thioethers

Info

Publication number: CA1068605A
Authority: CA; Canada
Prior art keywords: group; cells; cooh; composition according; sia
Prior art date: 1975-06-09
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

Application number

CA254,477A

Other languages

English (en)

Inventor

Malka Robert-Gero

Philippe Vigier

Edgar Lederer

Constantin Bona

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bpifrance Financement SA

Original Assignee

Agence National de Valorisation de la Recherche ANVAR

Priority date (The priority date 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 date listed.)

1975-06-09

Filing date

1976-06-09

Publication date

1979-12-25

1976-06-09 Application filed by Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR

1979-12-25 Application granted granted Critical

1979-12-25 Publication of CA1068605A publication Critical patent/CA1068605A/fr

Status Expired legal-status Critical Current

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)

CA254,477A 1975-06-09 1976-06-09 Medicament a base d'adenosine 5'-thioethers Expired CA1068605A (fr)

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 (fr)	1979-12-25

Family

ID=9156224

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA254,477A Expired CA1068605A (fr)	1975-06-09	1976-06-09	Medicament a base d'adenosine 5'-thioethers

Country Status (6)

Country	Link
JP (1)	JPS52125633A (fr)
CA (1)	CA1068605A (fr)
DE (1)	DE2625835A1 (fr)
FR (1)	FR2313937A1 (fr)
GB (1)	GB1555991A (fr)
OA (1)	OA05351A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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.
DE69825288D1 (de) *	1997-08-07	2004-09-02	Univ Utah	Prodrugs und konjugate von selenolenthaltenden verbindungen und ihre verwendung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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
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/fr unknown
- 1976-06-09 CA CA254,477A patent/CA1068605A/fr not_active Expired
- 1976-06-09 DE DE19762625835 patent/DE2625835A1/de not_active Ceased

Also Published As

Publication number	Publication date
GB1555991A (en)	1979-11-14
DE2625835A1 (de)	1976-12-23
FR2313937B1 (fr)	1978-10-06
FR2313937A1 (fr)	1977-01-07
JPS52125633A (en)	1977-10-21
OA05351A (fr)	1981-02-28

Publication	Publication Date	Title
RU2139884C1 (ru)	1999-10-20	Моноэфирные соединения, фармацевтическая композиция
HIRABAYASHI et al.	1991	Antiviral activities of glycyrrhizin and its modified compounds against human immunodeficiency virus type 1 (HIV-1) and herpes simplex virus type 1 (HSV-1) in vitro
FI105035B (fi)	2000-05-31	Menetelmä uuden, terapeuttisesti aktiivisen monoesteriyhdisteen valmistamiseksi
KR910006271A (ko)	1991-04-29	인돌-, 벤조푸란-, 및 벤조티오펜-함유 리폭시 게나제-억제 화합물
KR930006045A (ko)	1993-04-20	항종양 활성을 가진 피리미딘 뉴클레오사이드, 그의 제조방법 및 용도
Van Duuren et al.	1968	Tumor-promoting agents from Croton tiglium L. and their mode of action
Pegg	1971	Studies on inhibitors of mammalian tRNA methylases
Wnuk et al.	1997	Anticancer and antiviral effects and inactivation of S-adenosyl-l-homocysteine hydrolase with 5 ‘-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues
Kaukel et al.	1972	Divergent action of cAMP and dibutyryl cAMP on macromolecular synthesis in HeLa S3 cultures
WO1991013898A1 (fr)	1991-09-19	Composes de o6-guanine benzylee, guanosine et de 2'-desoxyguanine ayant une activite d'appauvrissement de o6-alkylguanine-adn alkyltransferase
SE8204918L (sv)	1983-04-28	Nya 3-amino-pregn-5-en-derivat, deras salter, sett for framstellning och anvendning derav som lekemedel och kompositioner innehallande dem
Wolfson et al.	1986	Neplanocin A. Actions on S-adenosylhomocysteine hydrolase and on hormone synthesis by GH4C1 cells.
FR2683818B1 (fr)	1993-12-31	Nouveaux derives de 3-sulfonylamino-2-(1h)-quinoleinone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
KR0135723B1 (ko)	1998-04-23	신규한 에스큘레틴 유도체 및 약학 조성물
US4148888A (en)	1979-04-10	3-Deazaadenosine as an inhibitor of adenosylhomocysteine hydrolase with antiviral activity
KR880000432A (ko)	1988-03-25	4(3H)-옥소-5,6,7,8-테트라히드로피리도-2,3-d 피리미딘 유도체
JPH0267218A (ja)	1990-03-07	ウイルス・ゲノム不活化剤
Evans et al.	1977	The activity of the pyrimidine biosynthetic pathway in MGH-U1 transitional carcinoma cells grown in tissue culture
HUP0001827A2 (hu)	2001-05-28	Kolchicin-származékok, eljárás előállításukra, valamint ezeket tartalmazó gyógyszerkészítmények, és a vegyületek alkalmazása gyógyszerkészítmények előállítására
SUZUKI et al.	1976	Antitumor activity of derivatives of mycophenolic acid
FR2707089B1 (fr)	1995-08-18	Nouveaux dérivés d'acide phosphonique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
Mirkin et al.	1987	Cytotoxic action of adenosine nucleoside and dialdehyde analogues on murine neuroblastoma in tissue culture: structure-activity relationships
ES386297A1 (es)	1973-03-16	Procedimiento para la preparacion de derivados de evomono- sido.
Reese et al.	1985	Control of growth, morphology, and alkaline phosphatase activity by butyrate and related short-chain fatty acids in the retinoid-responsive 9-1C rat prostatic adenocarcinoma cell
GB1159571A (en)	1969-07-30	Improvements in or relating to Nucleoside Derivatives and the manufacture thereof