CA1294572C - Compose a base d'hypoxanthine, son utilisation et procede pour sa production - Google Patents

Compose a base d'hypoxanthine, son utilisation et procede pour sa production

Info

Publication number: CA1294572C
Authority: CA; Canada
Prior art keywords: compound; formula; following formula; base represented; ifo
Prior art date: 1987-05-28
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

Application number

CA000538274A

Other languages

English (en)

Inventor

Nobuyoshi Shimada

Takayuki Tomizawa

Shigeru Hasegawa

Kaoru Matsuo

Hiroo Hoshino

Akio Fujii

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.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

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.)

1987-05-28

Filing date

1987-05-28

Publication date

1992-01-21

1987-05-28 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1987-05-28 Priority to CA000538274A priority Critical patent/CA1294572C/fr

1992-01-21 Application granted granted Critical

1992-01-21 Publication of CA1294572C publication Critical patent/CA1294572C/fr

2009-01-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 60
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims abstract description 16
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 title claims abstract description 9
230000008569 process Effects 0.000 title claims abstract description 6
244000005700 microbiome Species 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 12
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 claims description 8
101710169336 5'-deoxyadenosine deaminase Proteins 0.000 claims description 7
102000055025 Adenosine deaminases Human genes 0.000 claims description 7
241000725303 Human immunodeficiency virus Species 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 5
239000003443 antiviral agent Substances 0.000 claims description 5
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 4
229960005305 adenosine Drugs 0.000 claims description 4
239000003018 immunosuppressive agent Substances 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
229930024421 Adenine Natural products 0.000 claims description 2
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 2
229960000643 adenine Drugs 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000007853 buffer solution Substances 0.000 claims 2
239000008055 phosphate buffer solution Substances 0.000 claims 1
229940079593 drug Drugs 0.000 abstract description 8
239000003814 drug Substances 0.000 abstract description 8
230000000840 anti-viral effect Effects 0.000 abstract description 6
230000001506 immunosuppresive effect Effects 0.000 abstract description 6
210000004027 cell Anatomy 0.000 description 16
239000000047 product Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
241000588724 Escherichia coli Species 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
241000700605 Viruses Species 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
229940088598 enzyme Drugs 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
108010062580 Concanavalin A Proteins 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
230000000120 cytopathologic effect Effects 0.000 description 4
230000018109 developmental process Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000000243 solution Substances 0.000 description 4
208000030507 AIDS Diseases 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000228150 Penicillium chrysogenum Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
239000000427 antigen Substances 0.000 description 3
108091007433 antigens Proteins 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
230000035584 blastogenesis Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229960003444 immunosuppressant agent Drugs 0.000 description 3
230000001861 immunosuppressant effect Effects 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
LMJVXGOFWKVXAW-OXOINMOOSA-N oxetanocin A Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@H]1CO LMJVXGOFWKVXAW-OXOINMOOSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000002054 transplantation Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
OLXZPDWKRNYJJZ-UHFFFAOYSA-N 5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol Chemical compound C1=NC=2C(N)=NC=NC=2N1C1CC(O)C(CO)O1 OLXZPDWKRNYJJZ-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
241000588919 Citrobacter freundii Species 0.000 description 2
241000221779 Fusarium sambucinum Species 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
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 2
241000588772 Morganella morganii Species 0.000 description 2
241000187678 Nocardia asteroides Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000187747 Streptomyces Species 0.000 description 2
241000913727 Streptomyces alboniger Species 0.000 description 2
241000958262 Streptomyces californicus Species 0.000 description 2
241000970242 Streptomyces chrestomyceticus Species 0.000 description 2
241000218527 Streptomyces tubercidicus Species 0.000 description 2
241001147844 Streptomyces verticillus Species 0.000 description 2
230000009102 absorption Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000009471 action Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000013065 commercial product Substances 0.000 description 2
239000012531 culture fluid Substances 0.000 description 2
238000012258 culturing Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000002649 immunization Methods 0.000 description 2
239000008101 lactose Substances 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
150000007523 nucleic acids Chemical class 0.000 description 2
102000039446 nucleic acids Human genes 0.000 description 2
108020004707 nucleic acids Proteins 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002212 purine nucleoside Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
230000003612 virological effect Effects 0.000 description 2
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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
229930191892 Formycin Natural products 0.000 description 1
KBHMEHLJSZMEMI-UHFFFAOYSA-N Formycin A Natural products N1N=C2C(N)=NC=NC2=C1C1OC(CO)C(O)C1O KBHMEHLJSZMEMI-UHFFFAOYSA-N 0.000 description 1
206010019799 Hepatitis viral Diseases 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
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 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
208000029462 Immunodeficiency disease Diseases 0.000 description 1
102000016943 Muramidase Human genes 0.000 description 1
108010014251 Muramidase Proteins 0.000 description 1
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
LMJVXGOFWKVXAW-UHFFFAOYSA-N Oxetanocin Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C1CO LMJVXGOFWKVXAW-UHFFFAOYSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
241000700584 Simplexvirus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
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 1
239000002253 acid Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000002411 adverse Effects 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000004748 cultured cell Anatomy 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
VEPYXRRTOARCQD-IGPDFVGCSA-N formycin Chemical compound N1=N[C]2C(N)=NC=NC2=C1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O VEPYXRRTOARCQD-IGPDFVGCSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000007475 hemolytic anemia Diseases 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000004325 lysozyme Substances 0.000 description 1
229960000274 lysozyme Drugs 0.000 description 1
235000010335 lysozyme Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
206010028417 myasthenia gravis Diseases 0.000 description 1
MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000008213 purified water Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
210000004989 spleen cell Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000538274A 1987-05-28 1987-05-28 Compose a base d'hypoxanthine, son utilisation et procede pour sa production Expired - Lifetime CA1294572C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000538274A CA1294572C (fr)	1987-05-28	1987-05-28	Compose a base d'hypoxanthine, son utilisation et procede pour sa production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000538274A CA1294572C (fr)	1987-05-28	1987-05-28	Compose a base d'hypoxanthine, son utilisation et procede pour sa production

Publications (1)

Publication Number	Publication Date
CA1294572C true CA1294572C (fr)	1992-01-21

Family

ID=4135766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000538274A Expired - Lifetime CA1294572C (fr)	1987-05-28	1987-05-28	Compose a base d'hypoxanthine, son utilisation et procede pour sa production

Country Status (1)

Country	Link
CA (1)	CA1294572C (fr)

1987
- 1987-05-28 CA CA000538274A patent/CA1294572C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1994-07-23	MKLA	Lapsed

Publication	Publication Date	Title
US4845215A (en)	1989-07-04	Purine derivative
EP0182315B1 (fr)	1989-04-05	Antibiotique NK84-0218, compositions pharmaceutiques le contenant et procédé pour sa production
CA1304365C (fr)	1992-06-30	Oxetanocines
US4163780A (en)	1979-08-07	Ks-2-a
EP0351799A2 (fr)	1990-01-24	Antibiotiques antifongiques
JPH0219320A (ja)	1990-01-23	新規免疫抑制剤
KR940005658B1 (ko)	1994-06-22	히포크산틴 염기(hypoxanthine base)를 가진 신규 화합물 및 제조방법
CA1263946A (fr)	1989-12-19	Composes de 7-hydroxyguanine, procede de preparation et agent anti-tumoral les contenant
JPH01246297A (ja)	1989-10-02	ベータ―２’，２’―ジフルオロヌクレオシド類の製造方法
CA2020800A1 (fr)	1991-01-11	Antibiotique bu-3889v antiviral
US5236930A (en)	1993-08-17	Oxazopyrroloquinolines and use of oxazopyrroloquinolines
CA1113950A (fr)	1981-12-08	Isofortimicine
US3892732A (en)	1975-07-01	Antibiotic tuberactinomycin-N and process for production thereof
US6004995A (en)	1999-12-21	Macrolide compound 0406
US4563462A (en)	1986-01-07	Substance AX-2, a process for producing the same and an antitumor composition containing the same
US3923979A (en)	1975-12-02	Antibiotic 60-6 and production thereof
EP0289354A2 (fr)	1988-11-02	L'antibiotique TAN-950A, sa production et son utilisation
JP3688446B2 (ja)	2005-08-31	新規テルペン系化合物０４０６ｔｐ−１
Albu et al.	1963	Studies in the biosynthesis of fungal metabolites. 5. The utilization of sulphur-containing amino acids as penicillin side-chain precursors
JPH01216927A (ja)	1989-08-30	抗腫瘍剤
JPS63157992A (ja)	1988-06-30	抗生物質ｎ−ヒドロキシジヒドロアビコビロマイシン
JPH0770164A (ja)	1995-03-14	生理活性物質ｔａｎ−１７１３、その製造法および用途
JPWO1995007288A1 (ja)	1996-01-23	抗レトロウイルス物質プロヒビシンおよびそれを産生する微生物
JPS59204199A (ja)	1984-11-19	抗菌性増強物質ｆ６およびその製造法
JPH06343480A (ja)	1994-12-20	Ｓｆ２３１５ａの製造法及びその薬学的用途