JPH0246599B2 - - Google Patents
Info
- Publication number
- JPH0246599B2 JPH0246599B2 JP1022771A JP2277189A JPH0246599B2 JP H0246599 B2 JPH0246599 B2 JP H0246599B2 JP 1022771 A JP1022771 A JP 1022771A JP 2277189 A JP2277189 A JP 2277189A JP H0246599 B2 JPH0246599 B2 JP H0246599B2
- Authority
- JP
- Japan
- Prior art keywords
- mta
- sulfoxide
- methylthioadenosine
- deoxy
- aggregation
- 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 - Lifetime
Links
- WUUGFSXJNOTRMR-UHFFFAOYSA-N 5alpha-Hydroxy-3abeta,5beta,8-trimethyl-1-(1,5-dimethyl-hexen-(4)-yl)-4abetaH,7abetaH-dicyclopentano[a.d]cyclooctaen-(8) Natural products OC1C(O)C(CSC)OC1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-UHFFFAOYSA-N 0.000 claims description 51
- WUUGFSXJNOTRMR-IOSLPCCCSA-N 5'-S-methyl-5'-thioadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-IOSLPCCCSA-N 0.000 claims description 46
- 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 claims description 15
- 229960001570 ademetionine Drugs 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 11
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 10
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 10
- 102000008186 Collagen Human genes 0.000 description 9
- 108010035532 Collagen Proteins 0.000 description 9
- 229920001436 collagen Polymers 0.000 description 9
- -1 MTA sulfoxide Chemical class 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 6
- 230000002744 anti-aggregatory effect Effects 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 229940114079 arachidonic acid Drugs 0.000 description 6
- 235000021342 arachidonic acid Nutrition 0.000 description 6
- 230000001754 anti-pyretic effect Effects 0.000 description 5
- 231100001274 therapeutic index Toxicity 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 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 4
- 230000000202 analgesic effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 210000000416 exudates and transudate Anatomy 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229960000905 indomethacin Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003568 thioethers Chemical class 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229960000212 aminophenazone Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- WXOJULRVRHWMGT-JLQSGANNSA-N 5'-deoxy-5'-(methylsulfinyl)adenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CS(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WXOJULRVRHWMGT-JLQSGANNSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IOYQOOUTHXXDIC-UHFFFAOYSA-N CSc1cccc(CC(C)N)c1 Chemical compound CSc1cccc(CC(C)N)c1 IOYQOOUTHXXDIC-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 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
- 238000001727 in vivo Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005253 yeast cell Anatomy 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21550/80A IT1193529B (it) | 1980-04-22 | 1980-04-22 | Derivati adenosinici ad attivita' antinfiammatoria ed analgesica e composizioni terapeutiche che li contengono come principio attivo |
| IT21550A/80 | 1980-04-22 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5930181A Division JPS56166117A (en) | 1980-04-22 | 1981-04-21 | Antiinflammatory and analgesic adenosine derivative and therapeutical composition containing it as effective component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01301692A JPH01301692A (ja) | 1989-12-05 |
| JPH0246599B2 true JPH0246599B2 (US20020051482A1-20020502-M00012.png) | 1990-10-16 |
Family
ID=11183457
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5930181A Granted JPS56166117A (en) | 1980-04-22 | 1981-04-21 | Antiinflammatory and analgesic adenosine derivative and therapeutical composition containing it as effective component |
| JP1022771A Granted JPH01301692A (ja) | 1980-04-22 | 1989-02-02 | ５’―デオキシ―５’―メチルチオアデノシンの新規な製造方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5930181A Granted JPS56166117A (en) | 1980-04-22 | 1981-04-21 | Antiinflammatory and analgesic adenosine derivative and therapeutical composition containing it as effective component |
Country Status (17)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1177373B (it) * | 1984-12-06 | 1987-08-26 | Bioresearch Spa | Sali della 5'-metiltio-5'-deossiadenosina con acidi solfonici a lunga catena alchilica |
| IT1227049B (it) * | 1988-07-29 | 1991-03-14 | Bioresearch Spa | Impiego di derivati adenosinici per la preparazione di composizioni farmaceutiche aventi attivita' immunostimolante. |
| JPH0497287A (ja) * | 1990-08-10 | 1992-03-30 | Nec Ic Microcomput Syst Ltd | 画像表示集積回路 |
| EP1891961B1 (en) * | 2005-03-17 | 2009-09-16 | Proyecto de Biomedicina Cima, S.L. | Use of 5'-methylthioadenosine (mta) in the prevention and/or treatment of autoimmune diseases and/or transplant rejection |
| ES2259552B1 (es) * | 2005-03-17 | 2007-06-16 | Proyecto De Biomedicina Cima, S.L. | Empleo de 5'-metiltioadenosina (mta) en la prevencion y/o tratamiento de enfermedades autoinmunes y/o rechazo de transplantes. |
| DE102010027595A1 (de) * | 2010-07-23 | 2012-01-26 | Helmut Vorbrüggen | Vermeidung von Ischämie- oder Degenerations-Schäden im Gehirn bei Anwendung von Adenosin-Derivaten |
| DE102011005232A1 (de) * | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| WO2014163151A1 (ja) * | 2013-04-05 | 2014-10-09 | ライオン株式会社 | 酵母培養物及び内服組成物 |
| WO2014163150A1 (ja) * | 2013-04-05 | 2014-10-09 | ライオン株式会社 | 内服組成物 |
| WO2014163152A1 (ja) * | 2013-04-05 | 2014-10-09 | ライオン株式会社 | ノンレム睡眠促進剤、深睡眠促進剤および自然睡眠誘発剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1259341B (de) * | 1962-12-22 | 1968-01-25 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung neuer 5'-Sulfoxyde von Nucleosiden |
| DE1545645A1 (de) * | 1965-12-06 | 1969-08-21 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung von disubstituierten Adenosin-Derivaten |
| GB1436509A (en) * | 1973-11-27 | 1976-05-19 | Ajinomoto Kk | Method for producing s-adenosylmethionine or methylthioadenosine from yeast |
| FR2313937A1 (fr) * | 1975-06-09 | 1977-01-07 | Anvar | Medicament a base de 5' thioethers de l'adenosine |
| FR2424027A1 (fr) * | 1978-04-28 | 1979-11-23 | Merieux Inst | Nouveau medicament, notamment sedatif et inducteur de sommeil et compositions pharmaceutiques la renfermant |
-
1980
- 1980-04-22 IT IT21550/80A patent/IT1193529B/it active
-
1981
- 1981-04-17 BE BE0/204529A patent/BE888472A/fr not_active IP Right Cessation
- 1981-04-21 SE SE8102489A patent/SE460198B/sv not_active IP Right Cessation
- 1981-04-21 CA CA000375784A patent/CA1198105A/en not_active Expired
- 1981-04-21 LU LU83307A patent/LU83307A1/fr unknown
- 1981-04-21 AR AR285020A patent/AR231144A1/es active
- 1981-04-21 NO NO811346A patent/NO150515C/no unknown
- 1981-04-21 JP JP5930181A patent/JPS56166117A/ja active Granted
- 1981-04-21 ES ES501539A patent/ES501539A0/es active Granted
- 1981-04-21 DK DK176481A patent/DK159453C/da not_active IP Right Cessation
- 1981-04-22 GB GB8112428A patent/GB2074446B/en not_active Expired
- 1981-04-22 CH CH4716/84A patent/CH650514A5/de not_active IP Right Cessation
- 1981-04-22 FI FI811249A patent/FI70227C/fi not_active IP Right Cessation
- 1981-04-22 DE DE19813116067 patent/DE3116067A1/de active Granted
- 1981-04-22 NL NL8101984A patent/NL192111C/nl not_active IP Right Cessation
- 1981-04-22 CH CH263281A patent/CH645544A5/de not_active IP Right Cessation
- 1981-04-22 FR FR8107992A patent/FR2491761A1/fr active Granted
-
1982
- 1982-04-01 ES ES511039A patent/ES8306378A1/es not_active Expired
-
1983
- 1983-08-15 GB GB08321947A patent/GB2144409B/en not_active Expired
-
1984
- 1984-05-25 GB GB08413454A patent/GB2144038B/en not_active Expired
-
1987
- 1987-03-04 SE SE8700914A patent/SE464635B/sv not_active IP Right Cessation
- 1987-03-04 SE SE8700913A patent/SE466238B/sv not_active IP Right Cessation
-
1989
- 1989-02-02 JP JP1022771A patent/JPH01301692A/ja active Granted
-
1992
- 1992-06-26 MX MX9203630A patent/MX9203630A/es unknown
Also Published As
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