HU193769B - Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections - Google Patents

Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections Download PDF

Info

Publication number: HU193769B
Authority: HU; Hungary
Prior art keywords: heparinate; heparin; solution; salt; sodium
Prior art date: 1985-06-04

Application number

HU852197A

Other languages

English (en)

Hungarian (hu)

Inventor

Gyoergy Kerey

Erzsebet Neszmelyi

Pal Gere

Janos Illes

Bela Stefko

Istvan Zambo

Original Assignee

Richter Gedeon Vegyeszet

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.)

1985-06-04

Filing date

1985-06-04

Publication date

1987-11-30

1985-06-04 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1985-06-04 Priority to HU852197A priority Critical patent/HU193769B/hu

1986-05-28 Priority to AT0144386A priority patent/AT397250B/de

1986-06-02 Priority to FR868607875A priority patent/FR2582657B1/fr

1986-06-03 Priority to BE0/216737A priority patent/BE904867A/fr

1986-06-04 Priority to IT20676/86A priority patent/IT1190124B/it

1986-06-04 Priority to GB8613593A priority patent/GB2176200B/en

1987-11-30 Publication of HU193769B publication Critical patent/HU193769B/hu

Links

229920000669 heparin Polymers 0.000 title claims abstract description 110
238000000034 method Methods 0.000 title claims description 42
239000007924 injection Substances 0.000 title claims description 5
238000002347 injection Methods 0.000 title claims description 5
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class 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 claims abstract description 79
239000000243 solution Substances 0.000 claims abstract description 33
239000007864 aqueous solution Substances 0.000 claims abstract description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
150000001768 cations Chemical class 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 20
239000003960 organic solvent Substances 0.000 claims abstract description 12
-1 quaternary ammonium halide Chemical class 0.000 claims abstract description 12
229910001385 heavy metal Inorganic materials 0.000 claims abstract description 5
229920001499 Heparinoid Polymers 0.000 claims abstract description 4
239000002554 heparinoid Substances 0.000 claims abstract description 4
238000005406 washing Methods 0.000 claims abstract description 3
229960002897 heparin Drugs 0.000 claims description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
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
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 13
229910052708 sodium Inorganic materials 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 13
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 12
239000002244 precipitate Substances 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
239000001110 calcium chloride Substances 0.000 claims description 8
229910001628 calcium chloride Inorganic materials 0.000 claims description 8
229910001415 sodium ion Inorganic materials 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
238000005342 ion exchange Methods 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
239000003146 anticoagulant agent Substances 0.000 claims description 4
229940127219 anticoagulant drug Drugs 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
238000010668 complexation reaction Methods 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
150000001412 amines Chemical group 0.000 claims 1
150000003863 ammonium salts Chemical class 0.000 claims 1
125000002091 cationic group Chemical group 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
150000003751 zinc Chemical class 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 15
239000011575 calcium Substances 0.000 abstract description 15
229910052791 calcium Inorganic materials 0.000 abstract description 15
239000012071 phase Substances 0.000 abstract description 10
239000008346 aqueous phase Substances 0.000 abstract description 9
239000012074 organic phase Substances 0.000 abstract description 2
238000011282 treatment Methods 0.000 abstract description 2
125000003277 amino group Chemical group 0.000 abstract 2
239000008367 deionised water Substances 0.000 abstract 1
229910021641 deionized water Inorganic materials 0.000 abstract 1
230000000694 effects Effects 0.000 description 20
239000000047 product Substances 0.000 description 14
238000005341 cation exchange Methods 0.000 description 8
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 7
238000000502 dialysis Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000002441 reversible effect Effects 0.000 description 6
238000000926 separation method Methods 0.000 description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
230000002427 irreversible effect Effects 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000002510 pyrogen Substances 0.000 description 3
125000001453 quaternary ammonium group Chemical group 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 2
229960001008 heparin sodium Drugs 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
238000005184 irreversible process Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000012528 membrane Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000004448 titration Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OHJKXVLJWUPWQG-PNRHKHKDSA-N Heparinsodiumsalt Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](O)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)[C@H](C(O)=O)O1 OHJKXVLJWUPWQG-PNRHKHKDSA-N 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
238000011281 clinical therapy Methods 0.000 description 1
238000005202 decontamination Methods 0.000 description 1
230000003588 decontaminative effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229940095529 heparin calcium Drugs 0.000 description 1
229940025770 heparinoids Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ZASOFMFAGALONO-UHFFFAOYSA-N n-ethoxyethanamine;hydrochloride Chemical compound Cl.CCNOCC ZASOFMFAGALONO-UHFFFAOYSA-N 0.000 description 1
230000014508 negative regulation of coagulation Effects 0.000 description 1
239000003186 pharmaceutical solution Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU852197A 1985-06-04 1985-06-04 Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections HU193769B (en)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
HU852197A HU193769B (en)	1985-06-04	1985-06-04	Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections
AT0144386A AT397250B (de)	1985-06-04	1986-05-28	Verfahren zur herstellung von heparinsalzen
FR868607875A FR2582657B1 (fr)	1985-06-04	1986-06-02	Procede de preparation de sels d'heparine
BE0/216737A BE904867A (fr)	1985-06-04	1986-06-03	Procede de preparation de sels d'heparine:
IT20676/86A IT1190124B (it)	1985-06-04	1986-06-04	Procedimento per la preparazione di sali di eparina
GB8613593A GB2176200B (en)	1985-06-04	1986-06-04	Process for the preparation of heparin salts

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852197A HU193769B (en)	1985-06-04	1985-06-04	Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections

Publications (1)

Publication Number	Publication Date
HU193769B true HU193769B (en)	1987-11-30

Family

ID=10958239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU852197A HU193769B (en)	1985-06-04	1985-06-04	Sodium-exchanging process for producing pharmaceutically acceptable heparinates applicable even for injections

Country Status (6)

Country	Link
AT (1)	AT397250B (fr)
BE (1)	BE904867A (fr)
FR (1)	FR2582657B1 (fr)
GB (1)	GB2176200B (fr)
HU (1)	HU193769B (fr)
IT (1)	IT1190124B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE8702254D0 (sv) *	1987-05-29	1987-05-29	Kabivitrum Ab	Novel heparin derivatives
US5264425A (en) *	1988-06-03	1993-11-23	Italfarmaco S.P.A.	Glycosaminoglycan salts and pharmaceutical compositions containing them
CN117088997B (zh) *	2023-07-17	2025-05-30	盐城凯利药业有限公司	一种肝素钠的制备工艺

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1013641B (de) *	1956-03-20	1957-08-14	Nordmark Werke Gmbh	Verfahren zur Reinigung von Heparin
GB904112A (en) *	1958-12-19	1962-08-22	Roussel Uclaf	Improvements in or relating to heparine and derivatives thereof
US2989438A (en) *	1958-12-29	1961-06-20	Roussel Uclaf	Process of purifying heparin, and product produced therefrom
US3058884A (en) *	1959-09-14	1962-10-16	Abbott Lab	Process for purifying heparin
US3160563A (en) *	1960-05-13	1964-12-08	Ormonoterapia Richter Spa	Purification of heaprin
US3342683A (en) *	1964-02-25	1967-09-19	Taiyo Gyogyo Kabushiki Kaisha	Heparin from whale tissue and method of preparing same
US3451996A (en) *	1968-02-12	1969-06-24	Thompson Farms Co	Method for the preparation of heparin
US3817831A (en) *	1973-01-10	1974-06-18	Wilson Pharm & Chem Corp	Process for production of alkali metal salt of heparin
GB2027728B (en) *	1978-08-08	1983-03-30	Choay Sa	Physiologically acceptable heparin
IT1141263B (it) *	1980-02-29	1986-10-01	Italfarmaco Spa	Metodo per la preparazione di eparinato di calcio

1985
- 1985-06-04 HU HU852197A patent/HU193769B/hu unknown
1986
- 1986-05-28 AT AT0144386A patent/AT397250B/de not_active IP Right Cessation
- 1986-06-02 FR FR868607875A patent/FR2582657B1/fr not_active Expired - Lifetime
- 1986-06-03 BE BE0/216737A patent/BE904867A/fr not_active IP Right Cessation
- 1986-06-04 IT IT20676/86A patent/IT1190124B/it active
- 1986-06-04 GB GB8613593A patent/GB2176200B/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2582657A1 (fr)	1986-12-05
ATA144386A (de)	1993-07-15
IT1190124B (it)	1988-02-10
GB2176200B (en)	1990-01-24
GB2176200A (en)	1986-12-17
GB8613593D0 (en)	1986-07-09
IT8620676A0 (it)	1986-06-04
IT8620676A1 (it)	1987-12-04
BE904867A (fr)	1986-10-01
FR2582657B1 (fr)	1991-12-13
AT397250B (de)	1994-02-25

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628

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US4021544A (en)	1977-05-03	Complement inhibitors
HK1003003B (en)	1998-09-30	Novel compositions containing hyaluronic acid associates and a process for preparing same
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Schubert et al.	1961	Interaction in solution of lysozyme with chondroitin sulfate and its parent Proteinpolysaccharide1
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CA2065806A1 (fr)	1992-10-13	Methode de preparation de l-carnitine a partir de sels d,l de carnitinenitrile
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AU687966B2 (en)	1998-03-05	Use of mono-3,6-anhydro-cyclodextrins for solubilising a hydrophobic compound and monitoring the purity of an enantiomer, and method for preparing said cyclodextrins
JPH07196702A (ja)	1995-08-01	多糖類硫酸エステル塩の製造方法
US3432525A (en)	1969-03-11	Process for the production of alkaline earth metal salts of tocopherol dibasic acid hemiesters