NO782648L - Cyklisk forbindelse. - Google Patents

Cyklisk forbindelse.

Info

Publication number: NO782648L
Authority: NO; Norway
Prior art keywords: methyl; isoguanosine; formula; compound; carried out
Prior art date: 1977-08-03

Application number

NO782648A

Other languages

English (en)

Norwegian (no)

Inventor

Richard Peter Gregson

Ronald James Quinn

Alan Frederick Cook

Original Assignee

Hoffmann La Roche

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.)

1977-08-03

Filing date

1978-08-02

Publication date

1979-02-06

1978-02-10 Priority claimed from US05/876,768 external-priority patent/US4148993A/en

1978-06-13 Priority claimed from GB7826761A external-priority patent/GB2001955A/en

1978-08-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1979-02-06 Publication of NO782648L publication Critical patent/NO782648L/no

Links

WRKSCDGOQXKDME-UHFFFAOYSA-N 1-methylisoguanosine Natural products CN1C(=O)Nc2c(ncn2C3OC(CO)C(O)C3O)C1=N WRKSCDGOQXKDME-UHFFFAOYSA-N 0.000 claims description 20
NGSRMSVXLUMDAX-KQYNXXCUSA-N 6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-2-one Chemical compound C12=NC(=O)N(C)C(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NGSRMSVXLUMDAX-KQYNXXCUSA-N 0.000 claims description 20
NGSRMSVXLUMDAX-UHFFFAOYSA-N Doridosine Natural products C12=NC(=O)N(C)C(N)=C2N=CN1C1OC(CO)C(O)C1O NGSRMSVXLUMDAX-UHFFFAOYSA-N 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 5
-1 methyl halide Chemical class 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 4
230000011987 methylation Effects 0.000 claims description 4
238000007069 methylation reaction Methods 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
238000004587 chromatography analysis Methods 0.000 claims description 3
239000000284 extract Substances 0.000 claims description 3
239000012022 methylating agents‎ Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
239000012535 impurity Substances 0.000 claims description 2
238000004255 ion exchange chromatography Methods 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
239000000463 material Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 6
239000006260 foam Substances 0.000 description 6
241000243142 Porifera Species 0.000 description 4
150000002460 imidazoles Chemical class 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052814 silicon oxide Inorganic materials 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000493556 Tedania Species 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
MIKUYHXYGGJMLM-UUOKFMHZSA-N Crotonoside Chemical group C1=NC2=C(N)NC(=O)N=C2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O MIKUYHXYGGJMLM-UUOKFMHZSA-N 0.000 description 2
MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000000287 crude extract Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
AJACDNCVEGIBNA-KQYNXXCUSA-N (2r,3r,4s,5r)-2-(6-amino-2-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(OC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O AJACDNCVEGIBNA-KQYNXXCUSA-N 0.000 description 1
RCKORMYVZULMHP-IOSLPCCCSA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-2-methoxyoxolane-3,4-diol Chemical compound C1=NC2=C(N)N=CN=C2N1[C@]1(OC)O[C@H](CO)[C@@H](O)[C@H]1O RCKORMYVZULMHP-IOSLPCCCSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
AJACDNCVEGIBNA-UHFFFAOYSA-N 2-Methoxyadenosine Natural products C12=NC(OC)=NC(N)=C2N=CN1C1OC(CO)C(O)C1O AJACDNCVEGIBNA-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000011149 active material Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000002959 anti-hypotensive effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, ***e
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07H19/052—Imidazole radicals

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Neurosurgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO782648A 1977-08-03 1978-08-02 Cyklisk forbindelse. NO782648L (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
LU77910		1977-08-03
US87676978A	1978-02-10	1978-02-10
US05/876,768 US4148993A (en)	1978-02-10	1978-02-10	Process to produce 1-methyl isoguanosine
GB7826761A GB2001955A (en)	1977-08-03	1978-06-13	1-Methyl-isoguanine

Publications (1)

Publication Number	Publication Date
NO782648L true NO782648L (no)	1979-02-06

Family

ID=27449076

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782648A NO782648L (no)	1977-08-03	1978-08-02	Cyklisk forbindelse.

Country Status (14)

Country	Link
EP (1)	EP0000770A3 (de)
JP (1)	JPS5448794A (de)
AU (1)	AU3840678A (de)
DE (1)	DE2833887A1 (de)
DK (1)	DK343578A (de)
ES (1)	ES472297A1 (de)
FI (1)	FI782298A (de)
FR (1)	FR2399441A1 (de)
IL (1)	IL55240A0 (de)
IT (1)	IT1202760B (de)
MC (1)	MC1200A1 (de)
NO (1)	NO782648L (de)
PT (1)	PT68377A (de)
SE (1)	SE7808350L (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108864234B (zh) *	2018-07-06	2020-06-26	厦门医学院	一种从皱瘤海鞘中分离肌苷的方法

1978
- 1978-07-20 FI FI782298A patent/FI782298A/fi not_active Application Discontinuation
- 1978-07-27 AU AU38406/78A patent/AU3840678A/en active Pending
- 1978-07-28 IL IL55240A patent/IL55240A0/xx unknown
- 1978-07-31 MC MC781317A patent/MC1200A1/xx unknown
- 1978-08-01 JP JP9323178A patent/JPS5448794A/ja active Pending
- 1978-08-02 ES ES472297A patent/ES472297A1/es not_active Expired
- 1978-08-02 DK DK343578A patent/DK343578A/da unknown
- 1978-08-02 DE DE19782833887 patent/DE2833887A1/de not_active Withdrawn
- 1978-08-02 PT PT68377A patent/PT68377A/pt unknown
- 1978-08-02 SE SE7808350A patent/SE7808350L/xx unknown
- 1978-08-02 NO NO782648A patent/NO782648L/no unknown
- 1978-08-02 EP EP78100579A patent/EP0000770A3/de not_active Withdrawn
- 1978-08-03 IT IT26445/78A patent/IT1202760B/it active
- 1978-08-03 FR FR7822976A patent/FR2399441A1/fr active Pending

Also Published As

Publication number	Publication date
PT68377A (en)	1978-09-01
AU3840678A (en)	1980-01-31
IL55240A0 (en)	1978-09-29
EP0000770A2 (de)	1979-02-21
IT1202760B (it)	1989-02-09
MC1200A1 (fr)	1979-03-19
DK343578A (da)	1979-02-04
EP0000770A3 (de)	1979-06-13
ES472297A1 (es)	1979-02-16
SE7808350L (sv)	1979-02-04
JPS5448794A (en)	1979-04-17
FR2399441A1 (fr)	1979-03-02
DE2833887A1 (de)	1979-02-22
FI782298A (fi)	1979-02-04
IT7826445A0 (it)	1978-08-03

Publication	Publication Date	Title
DE2539963C2 (de)	1987-01-22	Purinverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten
DE69219807T2 (de)	1997-09-25	Thienopyridinderivate und diese enthaltende pharmazeutische Zubereitungen
SK99795A3 (en)	1995-12-06	Imidazopyrimidines, method of their preparation, treating with their contents and use
US5229378A (en)	1993-07-20	Glycyrrhetic acid derivatives
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