SE446301B - Medicin innehallande para-aminobensoesyra-n-d-xylosid sasom aktiv bestandsdel - Google Patents

Medicin innehallande para-aminobensoesyra-n-d-xylosid sasom aktiv bestandsdel

Info

Publication number: SE446301B
Authority: SE; Sweden
Prior art keywords: active compound; effect; xyloside; compound; animals
Prior art date: 1978-05-26

Application number

SE7904485A

Other languages

English (en)

Swedish (sv)

Other versions

SE7904485L (sv

Inventor

C Yoshikumi

Y Ohmura

F Hirose

M Ikuzawa

K Matsunaga

T Fujii

M Ohhara

T Ando

Original Assignee

Kureha Chemical Ind 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.)

1978-05-26

Filing date

1979-05-22

Publication date

1986-09-01

1978-05-26 Priority claimed from JP6314678A external-priority patent/JPS54154729A/ja

1978-12-29 Priority claimed from JP16138578A external-priority patent/JPS5924966B2/ja

1978-12-29 Priority claimed from JP53161386A external-priority patent/JPS5924965B2/ja

1979-05-22 Application filed by Kureha Chemical Ind Co Ltd filed Critical Kureha Chemical Ind Co Ltd

1979-11-27 Publication of SE7904485L publication Critical patent/SE7904485L/xx

1986-09-01 Publication of SE446301B publication Critical patent/SE446301B/sv

Links

239000004480 active ingredient Substances 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims description 76
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 18
239000011734 sodium Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 16
229910052708 sodium Inorganic materials 0.000 claims description 15
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 claims description 13
229960004050 aminobenzoic acid Drugs 0.000 claims description 8
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 5
208000002193 Pain Diseases 0.000 claims description 4
230000036407 pain Effects 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 3
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
206010037660 Pyrexia Diseases 0.000 claims description 2
230000027950 fever generation Effects 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 1
201000005577 familial hyperlipidemia Diseases 0.000 claims 1
201000001421 hyperglycemia Diseases 0.000 claims 1
208000027866 inflammatory disease Diseases 0.000 claims 1
241001465754 Metazoa Species 0.000 description 28
239000003814 drug Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 18
241000700159 Rattus Species 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 14
230000002401 inhibitory effect Effects 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 11
210000004369 blood Anatomy 0.000 description 11
239000008280 blood Substances 0.000 description 11
238000002474 experimental method Methods 0.000 description 11
229920001817 Agar Polymers 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
239000008272 agar Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
230000000202 analgesic effect Effects 0.000 description 8
230000001754 anti-pyretic effect Effects 0.000 description 8
239000012153 distilled water Substances 0.000 description 8
230000003276 anti-hypertensive effect Effects 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000012010 growth Effects 0.000 description 6
239000002504 physiological saline solution Substances 0.000 description 6
206010018691 Granuloma Diseases 0.000 description 5
241001494479 Pecora Species 0.000 description 5
206010070834 Sensitisation Diseases 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
230000036772 blood pressure Effects 0.000 description 5
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
210000003743 erythrocyte Anatomy 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
230000008313 sensitization Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 4
240000004808 Saccharomyces cerevisiae Species 0.000 description 4
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000007059 acute toxicity Effects 0.000 description 4
231100000403 acute toxicity Toxicity 0.000 description 4
206010003246 arthritis Diseases 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
239000002609 medium Substances 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000003826 tablet Substances 0.000 description 4
230000001875 tumorinhibitory effect Effects 0.000 description 4
LYAHJFZLDZDIOH-VURMDHGXSA-N (Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide Chemical compound C=1C=COC=1/C(C(=O)N)=C/C1=CC=C([N+]([O-])=O)O1 LYAHJFZLDZDIOH-VURMDHGXSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
244000063299 Bacillus subtilis Species 0.000 description 3
235000014469 Bacillus subtilis Nutrition 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
229920001525 carrageenan Polymers 0.000 description 3
235000010418 carrageenan Nutrition 0.000 description 3
230000010030 glucose lowering effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000007886 mutagenicity Effects 0.000 description 3
231100000299 mutagenicity Toxicity 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
230000001766 physiological effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000006798 recombination Effects 0.000 description 3
238000005215 recombination Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
XETSAYZRDCRPJY-UHFFFAOYSA-M sodium;4-aminobenzoate Chemical compound [Na+].NC1=CC=C(C([O-])=O)C=C1 XETSAYZRDCRPJY-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
210000003462 vein Anatomy 0.000 description 3
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
241000233866 Fungi Species 0.000 description 2
102000004877 Insulin Human genes 0.000 description 2
108090001061 Insulin Proteins 0.000 description 2
102000007330 LDL Lipoproteins Human genes 0.000 description 2
108010007622 LDL Lipoproteins Proteins 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
206010030113 Oedema Diseases 0.000 description 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000036592 analgesia Effects 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000008298 dragée Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
230000035931 haemagglutination Effects 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229940125396 insulin Drugs 0.000 description 2
229930027917 kanamycin Natural products 0.000 description 2
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 2
229960000318 kanamycin Drugs 0.000 description 2
229930182823 kanamycin A Natural products 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229960004857 mitomycin Drugs 0.000 description 2
230000000324 neuroprotective effect Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
229920002451 polyvinyl alcohol Polymers 0.000 description 2
239000013641 positive control Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000008439 repair process Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
238000002054 transplantation Methods 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
241001155961 Baris Species 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
240000001624 Espostoa lanata Species 0.000 description 1
235000009161 Espostoa lanata Nutrition 0.000 description 1
241000116710 Ferula foetidissima Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010053759 Growth retardation Diseases 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000000114 Pain Threshold Diseases 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
239000006159 Sabouraud's agar Substances 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
208000006268 Sarcoma 180 Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000004520 agglutination Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
-1 ampoules Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000002924 anti-infective effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
210000001099 axilla Anatomy 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229960002685 biotin Drugs 0.000 description 1
235000020958 biotin Nutrition 0.000 description 1
239000011616 biotin Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000007969 cellular immunity Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013068 control sample Substances 0.000 description 1
229940117173 croton oil Drugs 0.000 description 1
230000002950 deficient Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000499 gel Substances 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
239000008103 glucose Substances 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
230000004727 humoral immunity Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
230000035772 mutation Effects 0.000 description 1
239000013642 negative control Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
230000037040 pain threshold Effects 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940088417 precipitated calcium carbonate Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SE7904485A 1978-05-26 1979-05-22 Medicin innehallande para-aminobensoesyra-n-d-xylosid sasom aktiv bestandsdel SE446301B (sv)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP6314678A JPS54154729A (en)	1978-05-26	1978-05-26	Aminobenzoic acid derivative and drug preparation containing the same
JP16138578A JPS5924966B2 (ja)	1978-12-29	1978-12-29	アミノ安息香酸誘導体又はその医薬上許容される塩を有効成分とする抗炎症剤
JP53161386A JPS5924965B2 (ja)	1978-12-29	1978-12-29	アミノ安息香酸誘導体又はその医薬上許容し得る塩を有効成分とする解熱鎮痛剤

Publications (2)

Publication Number	Publication Date
SE7904485L SE7904485L (sv)	1979-11-27
SE446301B true SE446301B (sv)	1986-09-01

Family

ID=27298056

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7904485A SE446301B (sv)	1978-05-26	1979-05-22	Medicin innehallande para-aminobensoesyra-n-d-xylosid sasom aktiv bestandsdel

Country Status (8)

Country	Link
US (8)	US4559327A (de)
CH (2)	CH640412A5 (de)
DE (2)	DE2921328C3 (de)
FR (2)	FR2426468A1 (de)
GB (2)	GB2022411B (de)
IT (2)	IT1115239B (de)
PH (14)	PH14957A (de)
SE (1)	SE446301B (de)

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JPS5716898A (en) *	1980-07-03	1982-01-28	Kureha Chem Ind Co Ltd	Prostaglandin controller containing aminobenzoic derivative
SE446299B (sv) *	1978-04-11	1986-09-01	Kureha Chemical Ind Co Ltd	Medicinsk komposition innehallande ett derivat av para-aminobensoesyra som aktiv bestandsdel
US4637998A (en) *	1979-10-02	1987-01-20	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
JPS6041079B2 (ja) *	1979-12-14	1985-09-13	呉羽化学工業株式会社	オルト又はメタアミノ安息香酸誘導体
JPS5695197A (en) *	1979-12-28	1981-08-01	Kureha Chem Ind Co Ltd	Aminobenzoic acid derivative and physiologically active agent containing the same
JPS608000B2 (ja) *	1980-04-11	1985-02-28	呉羽化学工業株式会社	アミノフエニル誘導体及び該誘導体を含有する生理活性剤
EP0117413B1 (de) *	1980-12-09	1987-08-26	Seikagaku Kogyo Co. Ltd.	Verbindungen der D-Xylopyranosid-Serie und diese enthaltende therapeutische Zusammensetzungen
US5668117A (en) *	1991-02-22	1997-09-16	Shapiro; Howard K.	Methods of treating neurological diseases and etiologically related symptomology using carbonyl trapping agents in combination with previously known medicaments
USD418374S (en)	1998-07-30	2000-01-04	Aladdin Industries, Llc	Combined insulated beverage bottle and cups
US8980599B2 (en) *	2007-08-02	2015-03-17	Iogen Energy Corporation	Method for the production of alcohol from a pretreated lignocellulosic feedstock
US8710099B2 (en)	2009-09-10	2014-04-29	New York University	Treatment of cancer using the sodium salt of a benzoic acid derivative

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US2384102A (en) *	1943-09-30	1945-09-04	Hoffmann La Roche	Aromatic amine-n-pentapyranosides and process for the manufacture of same
US2659689A (en) *	1950-12-23	1953-11-17	Dyk & Company Inc Van	Benzoic esters
US2715123A (en) *	1951-11-15	1955-08-09	John E Hodge	Method for conducting the amadori rearrangement of n-glycosides
DE1793338A1 (de) *	1967-09-11	1972-01-27	Ciba Geigy Ag	Glucofuranoseverbindungen,Verfahren zu ihrer Herstellung und pharmazeutische Praeparate,gekennzeichnet durch einen Gehalt dieser Glucofuranoseverbindungen
IL37955A0 (en) *	1970-11-13	1971-12-29	Ciba Geigy Ag	O-esters of monosaccharides,their manufacture and pharmaceutical compositions containing them
CH597253A5 (de) *	1974-01-25	1978-03-31	Hoffmann La Roche
CH614720A5 (de) *	1974-10-15	1979-12-14	Asahi Chemical Ind
JPS5159880A (en) *	1974-11-22	1976-05-25	Asahi Chemical Ind	N44 ashirunukureoshidojikarubonsanesuteruno seiho
US3973007A (en) *	1975-05-15	1976-08-03	Milda Yanovna Pormale	High-molecular derivative of 2-dimethylaminoethyl ester of p-butylaminobenzoic acid, method for preparing same and application thereof
DE2535428A1 (de) *	1975-08-08	1977-02-24	Gruenenthal Chemie	Arzneimittel
DE2535429A1 (de) *	1975-08-08	1977-02-17	Gruenenthal Chemie	Arzneimittel
US4058550A (en) *	1975-10-28	1977-11-15	American Cyanamid Company	Polysubstituted-alkyl esters of 4-alkylaminobenzoic acids
US4440757A (en) *	1978-04-06	1984-04-03	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition comprising derivative of aminobenzoic acid for regulating prostaglandin
US4380536A (en) *	1978-04-06	1983-04-19	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing para-amino-benzoic acid-N-D-mannoside as an active ingredient
US4315921A (en) *	1978-04-06	1982-02-16	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing fara-amino-benzoic acid-N-D-xyloside as an active ingredient
US4322408A (en) *	1978-04-06	1982-03-30	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4313939A (en) *	1978-04-06	1982-02-02	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing para-aminobenzoic acid-N-L-rhamnoside as an active ingredient
US4322409A (en) *	1978-04-06	1982-03-30	Kureha Kagaku Kogyo Kabushiki Kaisha	Pharmaceutical composition containing a derivative of orthoaminobenzoic acid as an active ingredient
US4311694A (en) *	1979-12-31	1982-01-19	American Cyanamid Company	Amorphous coprecipitates of 4-(monoalkylamino) benzoic acid and derivatives and certain water-soluble materials
US4431939A (en) *	1981-07-28	1984-02-14	Rca Corporation	Structure and method for eliminating blocked apertures caused by charged particles

1979
- 1979-05-21 CH CH473679A patent/CH640412A5/de not_active IP Right Cessation
- 1979-05-21 CH CH471679A patent/CH640411A5/de not_active IP Right Cessation
- 1979-05-22 SE SE7904485A patent/SE446301B/sv not_active IP Right Cessation
- 1979-05-23 PH PH22543A patent/PH14957A/en unknown
- 1979-05-23 PH PH22542A patent/PH14542A/en unknown
- 1979-05-24 GB GB7918109A patent/GB2022411B/en not_active Expired
- 1979-05-24 IT IT22967/79A patent/IT1115239B/it active
- 1979-05-24 GB GB7918110A patent/GB2029698B/en not_active Expired
- 1979-05-24 IT IT22968/79A patent/IT1115238B/it active
- 1979-05-25 FR FR7913352A patent/FR2426468A1/fr active Granted
- 1979-05-25 DE DE2921328A patent/DE2921328C3/de not_active Expired
- 1979-05-25 DE DE2921327A patent/DE2921327C3/de not_active Expired
- 1979-05-25 FR FR7913351A patent/FR2426467A1/fr active Granted
1980
- 1980-01-04 PH PH23478A patent/PH14584A/en unknown
- 1980-01-04 PH PH23482A patent/PH14550A/en unknown
- 1980-01-04 PH PH23477A patent/PH14557A/en unknown
- 1980-01-04 PH PH23480A patent/PH14554A/en unknown
- 1980-01-04 PH PH23479A patent/PH14573A/en unknown
- 1980-01-04 PH PH23481A patent/PH14551A/en unknown
- 1980-09-16 PH PH24590A patent/PH16456A/en unknown
- 1980-09-16 PH PH24585A patent/PH14971A/en unknown
- 1980-09-16 PH PH24589A patent/PH16934A/en unknown
- 1980-09-16 PH PH24587A patent/PH20118A/en unknown
- 1980-09-16 PH PH24588A patent/PH16950A/en unknown
- 1980-09-16 PH PH24586A patent/PH15595A/en unknown
1983
- 1983-04-13 US US06/484,592 patent/US4559327A/en not_active Expired - Fee Related
1984
- 1984-02-29 US US06/584,629 patent/US4555505A/en not_active Expired - Fee Related
- 1984-12-27 US US06/686,670 patent/US4596794A/en not_active Expired - Fee Related
1985
- 1985-03-22 US US06/714,354 patent/US4801581A/en not_active Expired - Fee Related
- 1985-09-26 US US06/780,211 patent/US4649133A/en not_active Expired - Fee Related
- 1985-09-26 US US06/780,218 patent/US4663312A/en not_active Expired - Fee Related
1986
- 1986-11-24 US US06/931,974 patent/US4748159A/en not_active Expired - Fee Related
1987
- 1987-01-07 US US07/004,308 patent/US4757054A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FR2426467B1 (de)	1981-02-06
DE2921327A1 (de)	1979-12-06
US4748159A (en)	1988-05-31
DE2921328A1 (de)	1979-12-06
US4663312A (en)	1987-05-05
PH15595A (en)	1983-02-28
DE2921328C3 (de)	1982-03-25
US4649133A (en)	1987-03-10
CH640411A5 (de)	1984-01-13
FR2426468A1 (fr)	1979-12-21
US4801581A (en)	1989-01-31
US4555505A (en)	1985-11-26
SE7904485L (sv)	1979-11-27
PH16456A (en)	1983-10-13
DE2921328B2 (de)	1981-07-23
FR2426467A1 (fr)	1979-12-21
PH16934A (en)	1984-04-24
PH14551A (en)	1981-09-24
IT1115238B (it)	1986-02-03
PH14573A (en)	1981-09-24
IT7922968A0 (it)	1979-05-24
PH14584A (en)	1981-09-24
GB2029698B (en)	1982-10-27
PH14557A (en)	1981-09-24
US4757054A (en)	1988-07-12
DE2921327C3 (de)	1982-03-25
PH14971A (en)	1982-02-05
US4596794A (en)	1986-06-24
GB2022411B (en)	1982-10-20
IT7922967A0 (it)	1979-05-24
GB2022411A (en)	1979-12-19
FR2426468B1 (de)	1981-02-13
US4559327A (en)	1985-12-17
PH14554A (en)	1981-09-24
IT1115239B (it)	1986-02-03
CH640412A5 (de)	1984-01-13
PH20118A (en)	1986-10-02
GB2029698A (en)	1980-03-26
PH14542A (en)	1981-09-24
PH14957A (en)	1982-02-05
PH16950A (en)	1984-04-24
DE2921327B2 (de)	1981-08-06
PH14550A (en)	1981-09-24

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SE446299B (sv)	1986-09-01	Medicinsk komposition innehallande ett derivat av para-aminobensoesyra som aktiv bestandsdel
JPS6052157B2 (ja)	1985-11-18	スピロ−多環式イミダゾリジンジオン誘導体
SE448602B (sv)	1987-03-09	Medicinsk komposition innehallande ett derivat av ortoaminobensoesyra sasom aktiv bestandsdel
US4322408A (en)	1982-03-30	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4708950A (en)	1987-11-24	Pharmaceutical composition containing a derivative of orthoaminobenzoic acid as an active ingredient
SE446300B (sv)	1986-09-01	Medicinsk komposition innehallande para-aminobensoesyra-n-l-ramnosid sasom en aktiv bestandsdel
US4569842A (en)	1986-02-11	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4637998A (en)	1987-01-20	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4657895A (en)	1987-04-14	Pharmaceutical composition containing para-aminobenzoic acid-N-L-rhamnoside as an active ingredient
CA1158164A (en)	1983-12-06	Pharmaceutical composition containing para- aminobenzoic acid-n-d-mannoside as an active ingredient
CA1161363A (en)	1984-01-31	Pharmaceutical composition containing a derivative of ortho-aminobenzoic acid as an active ingredient
CA1158165A (en)	1983-12-06	Pharmaceutical composition containing para- aminobenzoic acid-n-d-xyloside as an active ingredient
US3574209A (en)	1971-04-06	Quaternary ammonium salts of methenamine
CA1158166A (en)	1983-12-06	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
BE875451A (fr)	1979-07-31	Nouveaux medicaments constitues de derives de l'acide p-amino-benzoique
JPS5924967B2 (ja)	1984-06-13	アミノ安息香酸誘導体を含有する抗糖尿病剤
BE876545A (fr)	1979-09-17	Composes de type acide p-aminobenzoique-n-d-xyloside utiles comme medicaments
JPH0142926B2 (de)	1989-09-18
JPS5835164B2 (ja)	1983-08-01	抗糖尿病剤
JPS5931735A (ja)	1984-02-20	２−（４−イソブチルフエニル）−１−プロパノ−ル３，４，５−トリメトキシベンゾエ−トおよびその製造法およびそれを有効成分とする医薬組成物