CA1338236C - Esters de l'acide alginique - Google Patents

Esters de l'acide alginique

Info

Publication number: CA1338236C
Authority: CA; Canada
Prior art keywords: alginic acid; total; insoluble; water; ester
Prior art date: 1986-06-30
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 - Fee Related

Application number

CA000616909A

Other languages

English (en)

Inventor

Francesco Della Valle

Aurelio Romeo

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.)

Fidia SpA

Original Assignee

Fidia SpA

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.)

1986-06-30

Filing date

1994-08-22

Publication date

1996-04-09

1986-06-30 Priority claimed from IT48201/86A external-priority patent/IT1203814B/it

1994-08-22 Application filed by Fidia SpA filed Critical Fidia SpA

1994-08-22 Priority to CA000616909A priority Critical patent/CA1338236C/fr

1996-04-09 Application granted granted Critical

1996-04-09 Publication of CA1338236C publication Critical patent/CA1338236C/fr

2007-06-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

235000010443 alginic acid Nutrition 0.000 title claims abstract description 433
229920000615 alginic acid Polymers 0.000 title claims abstract description 433
229960001126 alginic acid Drugs 0.000 title claims abstract description 409
239000000783 alginic acid Substances 0.000 title claims abstract description 408
150000004781 alginic acids Chemical class 0.000 title claims abstract description 337
150000002148 esters Chemical class 0.000 title claims abstract description 265
-1 heterocyclic alcohols Chemical class 0.000 claims abstract description 364
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 243
150000001298 alcohols Chemical class 0.000 claims abstract description 133
239000003814 drug Substances 0.000 claims abstract description 74
125000001931 aliphatic group Chemical group 0.000 claims abstract description 52
235000019441 ethanol Nutrition 0.000 claims description 288
238000000034 method Methods 0.000 claims description 122
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 118
238000002360 preparation method Methods 0.000 claims description 96
239000000203 mixture Substances 0.000 claims description 80
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 78
125000004432 carbon atom Chemical group C* 0.000 claims description 73
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 69
230000008569 process Effects 0.000 claims description 65
239000000825 pharmaceutical preparation Substances 0.000 claims description 55
125000000524 functional group Chemical group 0.000 claims description 53
239000008194 pharmaceutical composition Substances 0.000 claims description 44
239000013543 active substance Substances 0.000 claims description 38
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 36
239000012374 esterification agent Substances 0.000 claims description 35
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 33
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 32
150000003254 radicals Chemical class 0.000 claims description 32
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 31
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 31
229940079593 drug Drugs 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 21
229940088710 antibiotic agent Drugs 0.000 claims description 21
239000000546 pharmaceutical excipient Substances 0.000 claims description 21
239000003242 anti bacterial agent Substances 0.000 claims description 20
229960000890 hydrocortisone Drugs 0.000 claims description 20
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical group CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 20
125000002950 monocyclic group Chemical group 0.000 claims description 20
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 19
239000003960 organic solvent Substances 0.000 claims description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 16
239000002260 anti-inflammatory agent Substances 0.000 claims description 16
230000003110 anti-inflammatory effect Effects 0.000 claims description 16
QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 16
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 16
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 14
229940121363 anti-inflammatory agent Drugs 0.000 claims description 14
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 14
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 14
125000003367 polycyclic group Polymers 0.000 claims description 14
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
125000003438 dodecyl 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 description 13
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 12
125000004494 ethyl ester group Chemical group 0.000 claims description 12
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
150000004702 methyl esters Chemical class 0.000 claims description 12
125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 claims description 12
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 11
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 11
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 11
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 11
235000015165 citric acid Nutrition 0.000 claims description 11
229960004544 cortisone Drugs 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
125000002704 decyl 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])* 0.000 claims description 11
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 10
229940072056 alginate Drugs 0.000 claims description 10
239000003443 antiviral agent Substances 0.000 claims description 10
235000011187 glycerol Nutrition 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 10
229960005205 prednisolone Drugs 0.000 claims description 10
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
150000001241 acetals Chemical class 0.000 claims description 9
239000000674 adrenergic antagonist Substances 0.000 claims description 9
229930013930 alkaloid Natural products 0.000 claims description 9
229940121357 antivirals Drugs 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 9
229960001231 choline Drugs 0.000 claims description 9
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 9
229960003957 dexamethasone Drugs 0.000 claims description 9
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
150000003568 thioethers Chemical class 0.000 claims description 9
FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 claims description 8
CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 8
239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 8
239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 8
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims description 8
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 8
CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 8
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 8
HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 claims description 8
MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 claims description 8
KEVKXUZQHIMSCM-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanol Chemical compound CC(O)N1CCCC1 KEVKXUZQHIMSCM-UHFFFAOYSA-N 0.000 claims description 8
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 8
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 8
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 8
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 8
239000005792 Geraniol Substances 0.000 claims description 8
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 8
FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 claims description 8
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims description 8
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 8
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims description 8
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 claims description 8
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 8
230000003474 anti-emetic effect Effects 0.000 claims description 8
229940125681 anticonvulsant agent Drugs 0.000 claims description 8
239000001961 anticonvulsive agent Substances 0.000 claims description 8
229940125683 antiemetic agent Drugs 0.000 claims description 8
239000002111 antiemetic agent Substances 0.000 claims description 8
229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 claims description 8
229940034982 antineoplastic agent Drugs 0.000 claims description 8
239000002246 antineoplastic agent Substances 0.000 claims description 8
239000000164 antipsychotic agent Substances 0.000 claims description 8
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 8
239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 8
235000000484 citronellol Nutrition 0.000 claims description 8
239000003218 coronary vasodilator agent Substances 0.000 claims description 8
229930002886 farnesol Natural products 0.000 claims description 8
229940043259 farnesol Drugs 0.000 claims description 8
229940113087 geraniol Drugs 0.000 claims description 8
229960004275 glycolic acid Drugs 0.000 claims description 8
239000003326 hypnotic agent Substances 0.000 claims description 8
230000000147 hypnotic effect Effects 0.000 claims description 8
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
235000014655 lactic acid Nutrition 0.000 claims description 8
229930007744 linalool Natural products 0.000 claims description 8
239000001630 malic acid Substances 0.000 claims description 8
235000011090 malic acid Nutrition 0.000 claims description 8
229940035363 muscle relaxants Drugs 0.000 claims description 8
239000003158 myorelaxant agent Substances 0.000 claims description 8
WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 claims description 8
229950000688 phenothiazine Drugs 0.000 claims description 8
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 8
229920005989 resin Polymers 0.000 claims description 8
239000011975 tartaric acid Substances 0.000 claims description 8
235000002906 tartaric acid Nutrition 0.000 claims description 8
150000007970 thio esters Chemical class 0.000 claims description 8
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 8
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 8
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 claims description 7
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims description 7
229930194542 Keto Natural products 0.000 claims description 7
125000003158 alcohol group Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
229940035676 analgesics Drugs 0.000 claims description 7
239000000730 antalgic agent Substances 0.000 claims description 7
230000001088 anti-asthma Effects 0.000 claims description 7
230000000118 anti-neoplastic effect Effects 0.000 claims description 7
239000000924 antiasthmatic agent Substances 0.000 claims description 7
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WFPIAZLQTJBIFN-DVZOWYKESA-N zuclopenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(Cl)=CC=C2SC2=CC=CC=C2/1 WFPIAZLQTJBIFN-DVZOWYKESA-N 0.000 description 1

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CA000616909A 1986-06-30 1994-08-22 Esters de l'acide alginique Expired - Fee Related CA1338236C (fr)

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CA000616909A CA1338236C (fr)	1986-06-30	1994-08-22	Esters de l'acide alginique

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Application Number	Priority Date	Filing Date	Title
IT48201/86A IT1203814B (it)	1986-06-30	1986-06-30	Esteri dell'acido alginico
IT48201A/86		1986-06-30
CA000540467A CA1338235C (fr)	1986-06-30	1987-06-24	Esters de l'acide alginique
CA000616909A CA1338236C (fr)	1986-06-30	1994-08-22	Esters de l'acide alginique

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115850533A (zh) *	2022-09-28	2023-03-28	青岛格诚经纬生物科技有限公司	一种海藻酸材料及其制备方法、应用

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115850533A (zh) *	2022-09-28	2023-03-28	青岛格诚经纬生物科技有限公司	一种海藻酸材料及其制备方法、应用

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Date	Code	Title	Description
1999-04-09	MKLA	Lapsed

Publication	Publication Date	Title
CA1338235C (fr)	1996-04-09	Esters de l'acide alginique
US5122598A (en)	1992-06-16	Polysaccharide esters
US5416205A (en)	1995-05-16	New esters of alginic acid
EP0265116B1 (fr)	1998-03-11	Esters réticulés d'acide hyaluronique
CA1341276C (fr)	2001-07-31	Esters de l'acide hyaluronique et leurs sels
US5202431A (en)	1993-04-13	Partial esters of hyaluronic acid
US5676964A (en)	1997-10-14	Crosslinked carboxy polysaccharides
US5147861A (en)	1992-09-15	Esters of alginic acid
US5332809A (en)	1994-07-26	Partial esters of gellan
CA1338236C (fr)	1996-04-09	Esters de l'acide alginique
NZ235272A (en)	1992-03-26	Partial esters of alginic acid and their use in pharmaceuticals, sanitary articles, foods, textiles, printing and paper applications, and detergents

CA1338236C - Esters de l'acide alginique - Google Patents

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