CA1158164A - Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif - Google Patents

Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif

Info

Publication number: CA1158164A
Authority: CA; Canada
Prior art keywords: active ingredient; activity; mannoside; administration; composition according
Prior art date: 1980-10-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000363480A

Other languages

English (en)

Inventor

Chikao Yoshikumi

Yoshio Ohmura

Fumio Hirose

Minoru Ohhara

Masanori Ikuzawa

Kenichi Matsunaga

Takayoshi Fujii

Takao Ando

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.)

Kureha Corp

Original Assignee

Kureha Corp

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.)

1980-10-29

Filing date

1980-10-29

Publication date

1983-12-06

1980-10-29 Application filed by Kureha Corp filed Critical Kureha Corp

1980-10-29 Priority to CA000363480A priority Critical patent/CA1158164A/fr

1983-12-06 Application granted granted Critical

1983-12-06 Publication of CA1158164A publication Critical patent/CA1158164A/fr

Status Expired legal-status Critical Current

Links

239000004480 active ingredient Substances 0.000 title abstract description 69
239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 21
239000011734 sodium Substances 0.000 claims description 17
229910052708 sodium Inorganic materials 0.000 claims description 17
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 15
206010028980 Neoplasm Diseases 0.000 claims description 7
239000002504 physiological saline solution Substances 0.000 claims description 6
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 4
208000002193 Pain Diseases 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
230000036407 pain Effects 0.000 claims description 4
206010037660 Pyrexia Diseases 0.000 claims description 3
230000027950 fever generation Effects 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 2
238000007911 parenteral administration Methods 0.000 claims description 2
230000001944 accentuation Effects 0.000 claims 2
210000005036 nerve Anatomy 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
238000010255 intramuscular injection Methods 0.000 claims 1
238000010253 intravenous injection Methods 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
238000010254 subcutaneous injection Methods 0.000 claims 1
230000000694 effects Effects 0.000 description 29
238000000034 method Methods 0.000 description 23
241001465754 Metazoa Species 0.000 description 22
241000700159 Rattus Species 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
210000004369 blood Anatomy 0.000 description 13
239000008280 blood Substances 0.000 description 13
229920001817 Agar Polymers 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000008272 agar Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
230000001754 anti-pyretic effect Effects 0.000 description 8
239000013078 crystal Substances 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
241000699666 Mus <mouse, genus> Species 0.000 description 7
230000000202 analgesic effect Effects 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
230000000259 anti-tumor effect Effects 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
241001494479 Pecora Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000003276 anti-hypertensive effect Effects 0.000 description 5
238000003556 assay Methods 0.000 description 5
-1 benzoic ester Chemical class 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
239000008187 granular material Substances 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
206010018691 Granuloma Diseases 0.000 description 4
229930182474 N-glycoside Natural products 0.000 description 4
206010070834 Sensitisation Diseases 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
206010003246 arthritis Diseases 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
230000007886 mutagenicity Effects 0.000 description 4
231100000299 mutagenicity Toxicity 0.000 description 4
239000000376 reactant Substances 0.000 description 4
230000001603 reducing effect Effects 0.000 description 4
230000008313 sensitization Effects 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
208000011580 syndromic disease Diseases 0.000 description 4
239000003826 tablet Substances 0.000 description 4
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
206010030113 Oedema Diseases 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
229960004050 aminobenzoic acid Drugs 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
210000001072 colon Anatomy 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000001914 filtration Methods 0.000 description 3
230000012010 growth Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
230000001766 physiological effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
159000000000 sodium salts Chemical class 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
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 2
206010003445 Ascites Diseases 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
241000233866 Fungi Species 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
206010027476 Metastases Diseases 0.000 description 2
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 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
208000006268 Sarcoma 180 Diseases 0.000 description 2
208000005718 Stomach Neoplasms Diseases 0.000 description 2
206010042674 Swelling Diseases 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
230000008859 change Effects 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
230000008602 contraction Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
206010017758 gastric cancer Diseases 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
230000035931 haemagglutination Effects 0.000 description 2
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000001165 lymph node Anatomy 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000008188 pellet Substances 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920002451 polyvinyl alcohol Polymers 0.000 description 2
239000013641 positive control Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
230000013120 recombinational repair Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
201000011549 stomach cancer Diseases 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
230000002485 urinary effect Effects 0.000 description 2
208000006678 Abdominal Neoplasms Diseases 0.000 description 1
208000003200 Adenoma Diseases 0.000 description 1
206010001233 Adenoma benign Diseases 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
241000228245 Aspergillus niger Species 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
241000222122 Candida albicans Species 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
235000019227 E-number Nutrition 0.000 description 1
239000004243 E-number Substances 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
239000001828 Gelatine Substances 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
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 0.000 description 1
101100460719 Mus musculus Noto gene Proteins 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
241000191967 Staphylococcus aureus Species 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
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000004520 agglutination Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000005417 aminobenzoic acid derivatives Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 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
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
229940095731 candida albicans Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000007969 cellular immunity Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229940117173 croton oil Drugs 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
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000004727 humoral immunity Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
208000008384 ileus Diseases 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
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000033001 locomotion Effects 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
235000013372 meat Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 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
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
239000002304 perfume Substances 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229940088417 precipitated calcium carbonate Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000005549 size reduction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 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
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
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
210000003813 thumb Anatomy 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000363480A 1980-10-29 1980-10-29 Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif Expired CA1158164A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000363480A CA1158164A (fr)	1980-10-29	1980-10-29	Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000363480A CA1158164A (fr)	1980-10-29	1980-10-29	Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif

Publications (1)

Publication Number	Publication Date
CA1158164A true CA1158164A (fr)	1983-12-06

Family

ID=4118287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000363480A Expired CA1158164A (fr)	1980-10-29	1980-10-29	Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif

Country Status (1)

Country	Link
CA (1)	CA1158164A (fr)

1980
- 1980-10-29 CA CA000363480A patent/CA1158164A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-12-06	MKEX	Expiry

Publication	Publication Date	Title
US4673669A (en)	1987-06-16	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4757054A (en)	1988-07-12	Pharmaceutical composition containing para-amino-benzoic acid-N-D-xyloside as an active ingredient
US4372948A (en)	1983-02-08	Derivative of saccharide and physiologically active agent containing the same
FR2472561A1 (fr)	1981-07-03	Derives de l'acide 4-guanidinomethylcyclohexane carboxylique, leur procede de preparation et leur application en therapeutique
US4380536A (en)	1983-04-19	Pharmaceutical composition containing para-amino-benzoic acid-N-D-mannoside as an active ingredient
US4315921A (en)	1982-02-16	Pharmaceutical composition containing fara-amino-benzoic acid-N-D-xyloside as an active ingredient
US4322409A (en)	1982-03-30	Pharmaceutical composition containing a derivative of orthoaminobenzoic acid as an active ingredient
CA1158164A (fr)	1983-12-06	Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-mannoside comme ingredient actif
US4322408A (en)	1982-03-30	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4313939A (en)	1982-02-02	Pharmaceutical composition containing para-aminobenzoic acid-N-L-rhamnoside as an active ingredient
US4569842A (en)	1986-02-11	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
US4637998A (en)	1987-01-20	Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
US4450156A (en)	1984-05-22	Pharmaceutical composition containing a derivative of ortho-aminobenzoic acid as an active ingredient
SE448602B (sv)	1987-03-09	Medicinsk komposition innehallande ett derivat av ortoaminobensoesyra sasom aktiv bestandsdel
US4657895A (en)	1987-04-14	Pharmaceutical composition containing para-aminobenzoic acid-N-L-rhamnoside as an active ingredient
CA1158165A (fr)	1983-12-06	Compose pharmaceutique contenant de l'acide para- aminobenzoique-n-d-xyloside comme ingredient actif
CA1158166A (fr)	1983-12-06	Compose pharmaceutique contenant un derive de l'acide para-aminobenzoique comme ingredient actif
CA1158162A (fr)	1983-12-06	Composes pharmaceutiques contenant de l'acide para-aminobenzoique-n-l-rhamnoside comme ingredient actif
CA1161363A (fr)	1984-01-31	Compose pharmaceutique contenant un derive de l'acide ortho-aminobenzoique comme ingredient actif
GB2060636A (en)	1981-05-07	Esters of aminobenzoic acid, their preparation and compositions containing them
GB2060635A (en)	1981-05-07	Derivative of para- aminobenzoic acid, their preparation and use in pharmaceutical compositions
BE875451A (fr)	1979-07-31	Nouveaux medicaments constitues de derives de l'acide p-amino-benzoique
JPS6041079B2 (ja)	1985-09-13	オルト又はメタアミノ安息香酸誘導体
BE876544A (fr)	1979-09-17	Composes de type acide p-aminobenzoique-n-l-rhamnoside utiles comme medicaments