IL96441A - Polymers having an alkyl or troalkyl-aryl skeleton, processes for their preparation and pharmaceutical preparations containing them - Google Patents

Polymers having an alkyl or troalkyl-aryl skeleton, processes for their preparation and pharmaceutical preparations containing them

Info

Publication number: IL96441A
Authority: IL; Israel
Prior art keywords: compound according; compound; ring; aromatic ring; substituted
Prior art date: 1989-11-22

Application number

IL9644190A

Other languages

English (en)

Hebrew (he)

Other versions

IL96441A0 (en

Original Assignee

Rhone Poulenc Rorer Int

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.)

1989-11-22

Filing date

1990-11-22

Publication date

1995-01-24

1990-11-22 Application filed by Rhone Poulenc Rorer Int filed Critical Rhone Poulenc Rorer Int

1991-08-16 Publication of IL96441A0 publication Critical patent/IL96441A0/xx

1995-01-24 Publication of IL96441A publication Critical patent/IL96441A/en

Links

229920000642 polymer Polymers 0.000 title claims abstract description 188
238000000034 method Methods 0.000 title claims description 27
239000008194 pharmaceutical composition Substances 0.000 title claims description 16
230000008569 process Effects 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 93
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 20
238000004590 computer program Methods 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 90
239000000539 dimer Substances 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
229920002683 Glycosaminoglycan Polymers 0.000 claims description 25
-1 heteroalkyl aldehyde Chemical class 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 20
238000006471 dimerization reaction Methods 0.000 claims description 13
102000004169 proteins and genes Human genes 0.000 claims description 13
108090000623 proteins and genes Proteins 0.000 claims description 13
150000001491 aromatic compounds Chemical class 0.000 claims description 10
230000027455 binding Effects 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000000379 polymerizing effect Effects 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
108090000765 processed proteins & peptides Proteins 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
230000000975 bioactive effect Effects 0.000 claims description 7
102000004196 processed proteins & peptides Human genes 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000004404 heteroalkyl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
230000003278 mimic effect Effects 0.000 claims description 6
230000000144 pharmacologic effect Effects 0.000 claims description 6
125000000542 sulfonic acid group Chemical class 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
230000002429 anti-coagulating effect Effects 0.000 claims description 3
239000007862 dimeric product Substances 0.000 claims description 3
210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 2
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 111
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 51
235000011054 acetic acid Nutrition 0.000 description 37
230000000694 effects Effects 0.000 description 28
238000006116 polymerization reaction Methods 0.000 description 28
239000002253 acid Substances 0.000 description 24
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 21
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 18
235000019256 formaldehyde Nutrition 0.000 description 17
239000000178 monomer Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
229920000669 heparin Polymers 0.000 description 15
229960002897 heparin Drugs 0.000 description 15
239000000243 solution Substances 0.000 description 14
238000012360 testing method Methods 0.000 description 14
108010037536 heparanase Proteins 0.000 description 13
210000001519 tissue Anatomy 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
102100024025 Heparanase Human genes 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
239000012265 solid product Substances 0.000 description 12
108010013563 Lipoprotein Lipase Proteins 0.000 description 11
239000000047 product Substances 0.000 description 11
102000043296 Lipoprotein lipases Human genes 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
229910017974 NH40H Inorganic materials 0.000 description 9
238000005227 gel permeation chromatography Methods 0.000 description 9
230000014508 negative regulation of coagulation Effects 0.000 description 9
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
230000035602 clotting Effects 0.000 description 8
210000002808 connective tissue Anatomy 0.000 description 8
238000009826 distribution Methods 0.000 description 8
230000003993 interaction Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
206010053567 Coagulopathies Diseases 0.000 description 7
108050007372 Fibroblast Growth Factor Proteins 0.000 description 7
102000018233 Fibroblast Growth Factor Human genes 0.000 description 7
206010052428 Wound Diseases 0.000 description 7
208000027418 Wounds and injury Diseases 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
239000002585 base Substances 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
229940126864 fibroblast growth factor Drugs 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
238000003556 assay Methods 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
239000011707 mineral Substances 0.000 description 6
150000007524 organic acids Chemical class 0.000 description 6
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 5
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 5
230000003466 anti-cipated effect Effects 0.000 description 5
210000002744 extracellular matrix Anatomy 0.000 description 5
239000012458 free base Substances 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 4
MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
208000024172 Cardiovascular disease Diseases 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000003172 anti-dna Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000000470 constituent Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
150000002632 lipids Chemical class 0.000 description 4
230000001537 neural effect Effects 0.000 description 4
WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000013638 trimer Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 3
CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
206010003210 Arteriosclerosis Diseases 0.000 description 3
230000004568 DNA-binding Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229920002971 Heparan sulfate Polymers 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000010100 anticoagulation Effects 0.000 description 3
208000011775 arteriosclerosis disease Diseases 0.000 description 3
210000002469 basement membrane Anatomy 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000835 fiber Substances 0.000 description 3
230000006870 function Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
229920001282 polysaccharide Polymers 0.000 description 3
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125000006239 protecting group Chemical group 0.000 description 3
239000000376 reactant Substances 0.000 description 3
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229960004889 salicylic acid Drugs 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
230000004797 therapeutic response Effects 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 2
BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 2
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
UXWHGEBSCAHINE-UHFFFAOYSA-N 2-hydroxy-2-phenoxyacetic acid Chemical compound OC(=O)C(O)OC1=CC=CC=C1 UXWHGEBSCAHINE-UHFFFAOYSA-N 0.000 description 2
LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical group OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 2
YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
RGHMISIYKIHAJW-UHFFFAOYSA-N 3,4-dihydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(O)=C1 RGHMISIYKIHAJW-UHFFFAOYSA-N 0.000 description 2
UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 2
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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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239000000020 Nitrocellulose Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102000016611 Proteoglycans Human genes 0.000 description 2
108010067787 Proteoglycans Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 1
230000023597 hemostasis Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229920002674 hyaluronan Polymers 0.000 description 1
229960003160 hyaluronic acid Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000005027 hydroxyaryl group Chemical group 0.000 description 1
IAJILQKETJEXLJ-LECHCGJUSA-N iduronic acid Chemical compound O=C[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-LECHCGJUSA-N 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000003550 marker Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000001394 metastastic effect Effects 0.000 description 1
206010061289 metastatic neoplasm Diseases 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
XRAMJHXWXCMGJM-UHFFFAOYSA-N methyl 3-(4-hydroxyphenyl)propionate Chemical compound COC(=O)CCC1=CC=C(O)C=C1 XRAMJHXWXCMGJM-UHFFFAOYSA-N 0.000 description 1
CSKLFRWNGAHABI-UHFFFAOYSA-N methyl 3-[4-hydroxy-3-[[2-hydroxy-3-[[2-hydroxy-5-(3-methoxy-3-oxopropyl)phenyl]methyl]-5-(3-methoxy-3-oxopropyl)phenyl]methyl]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(CCC(=O)OC)C=3)O)C=C(CCC(=O)OC)C=2)O)=C1 CSKLFRWNGAHABI-UHFFFAOYSA-N 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
238000001471 micro-filtration Methods 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
201000000050 myeloid neoplasm Diseases 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
IBHWREHFNDMRPR-UHFFFAOYSA-N phloroglucinol carboxylic acid Natural products OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000007614 solvation Methods 0.000 description 1
241000894007 species Species 0.000 description 1
210000004989 spleen cell Anatomy 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000003765 sweetening 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
229940117972 triolein Drugs 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/18—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Polymers & Plastics (AREA)
Epidemiology (AREA)
Neurosurgery (AREA)
Hematology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Phenolic Resins Or Amino Resins (AREA)

IL9644190A 1989-11-22 1990-11-22 Polymers having an alkyl or troalkyl-aryl skeleton, processes for their preparation and pharmaceutical preparations containing them IL96441A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US44058689A	1989-11-22	1989-11-22
US44058489A	1989-11-22	1989-11-22

Publications (2)

Publication Number	Publication Date
IL96441A0 IL96441A0 (en)	1991-08-16
IL96441A true IL96441A (en)	1995-01-24

Family

ID=27032471

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9644190A IL96441A (en)	1989-11-22	1990-11-22	Polymers having an alkyl or troalkyl-aryl skeleton, processes for their preparation and pharmaceutical preparations containing them

Country Status (8)

Country	Link
EP (1)	EP0502117B1 (de)
JP (1)	JPH05508665A (de)
AT (1)	ATE181506T1 (de)
AU (1)	AU658133B2 (de)
CA (1)	CA2069448A1 (de)
DE (1)	DE69033182T2 (de)
IL (1)	IL96441A (de)
WO (1)	WO1991007183A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5409959A (en) *	1991-01-29	1995-04-25	Genelabs Incorporated	Antithrombotic treatment with calix(n)arene compounds
US5312837A (en) *	1991-01-29	1994-05-17	Genelabs Technologies, Inc.	Method of treating viral infections with aryl macrocyclic compounds
FR2672214A1 (fr) *	1991-01-31	1992-08-07	Rhone Poulenc Rorer Sa	Application de polymeres biologiquement actifs, pour l'obtention d'un medicament pour le traitement d'infections a retrovirus.
ATE216247T1 (de) *	1991-05-20	2002-05-15	Rhone Poulenc Rorer Internat H	Aromatische oligomere verbindungen als imitatoren bioaktives makromoleküle
WO2007131811A1 (de) *	2006-05-17	2007-11-22	Basf Se	Gemische von gerbstoffen, ihre herstellung und verwendung in arzneimitteln oder als desinfektionsmittel
EP2021010B1 (de)	2006-05-17	2014-04-23	Basf Se	Kondensationsprodukte, verfahren zu deren herstellung und deren verwendung in arzneimitteln, als desinfektionsmittel
US8945610B2 (en)	2007-11-14	2015-02-03	Basf Se	Condensation products based on bicyclic or polycyclic aromatics or heteroaromatics

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1344950A (en) *	1919-04-12	1920-06-29	Rohm & Haas	Tanning material and method of producing the same
US2097345A (en) *	1935-05-01	1937-10-26	Du Pont	Resinous composition
US2323481A (en) *	1939-03-14	1943-07-06	Du Pont	Chemical process and composition
US3035022A (en) *	1958-10-23	1962-05-15	Du Pont	New polymer compositions and process of preparation
DE1593876A1 (de) *	1967-06-03	1971-02-25	Bayer Ag	Verfahren zur Herstellung von Kondensationsprodukten
EP0354714A3 (de) *	1988-08-12	1991-04-10	Hadassah Medical Organization	Polyaromatische Verbindungen enthaltende pharmazeutische Zusammensetzungen

1990
- 1990-11-21 JP JP91501518A patent/JPH05508665A/ja active Pending
- 1990-11-21 EP EP91901098A patent/EP0502117B1/de not_active Expired - Lifetime
- 1990-11-21 CA CA002069448A patent/CA2069448A1/en not_active Abandoned
- 1990-11-21 AT AT91901098T patent/ATE181506T1/de not_active IP Right Cessation
- 1990-11-21 DE DE69033182T patent/DE69033182T2/de not_active Expired - Fee Related
- 1990-11-21 WO PCT/US1990/006847 patent/WO1991007183A1/en not_active Ceased
- 1990-11-21 AU AU69191/91A patent/AU658133B2/en not_active Ceased
- 1990-11-22 IL IL9644190A patent/IL96441A/en unknown

Also Published As

Publication number	Publication date
DE69033182T2 (de)	1999-10-28
AU6919191A (en)	1991-06-13
EP0502117B1 (de)	1999-06-23
AU658133B2 (en)	1995-04-06
JPH05508665A (ja)	1993-12-02
WO1991007183A1 (en)	1991-05-30
IL96441A0 (en)	1991-08-16
DE69033182D1 (de)	1999-07-29
EP0502117A4 (en)	1993-03-17
CA2069448A1 (en)	1991-05-23
EP0502117A1 (de)	1992-09-09
ATE181506T1 (de)	1999-07-15

Legal Events

Date	Code	Title	Description
1997-02-18	KB	Patent renewed
2001-04-30	KB	Patent renewed

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US5571506A (en)	1996-11-05	Aromatic oligomeric compounds useful as mimics of bioactive macromolecules
AU658133B2 (en)	1995-04-06	Polymers with alkyl- or heteroalkyl-aryl backbone and pharmaceutical compositions incorporating same
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Yildirim et al.	2016	End‐functionalized polylactides using a calcium‐based precatalyst: Synthesis and insights by mass spectrometry
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EP0585371B1 (de)	2002-04-17	Aromatische oligomere verbindungen als imitatoren bioaktives makromoleküle
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JPH10218902A (ja)	1998-08-18	低分子化硫酸化多糖、その製造法及び医薬組成物
EP0354714A2 (de)	1990-02-14	Polyaromatische Verbindungen enthaltende pharmazeutische Zusammensetzungen
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JPH03170435A (ja)	1991-07-24	ウイルス疾患の治療および予防用高分子電解質複合体
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