IE46005B1 - Preparations of 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoic acid and process for their manufacture - Google Patents

Preparations of 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoic acid and process for their manufacture

Info

Publication number: IE46005B1
Authority: IE; Ireland
Prior art keywords: particles; active substance; pharmaceutical preparation; coating; coated
Prior art date: 1976-12-07

Application number

IE2474/77A

Other languages

English (en)

Other versions

IE46005L (en

Original Assignee

Hoechst Ag

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.)

1976-12-07

Filing date

1977-12-06

Publication date

1983-01-26

1977-12-06 Application filed by Hoechst Ag filed Critical Hoechst Ag

1978-06-07 Publication of IE46005L publication Critical patent/IE46005L/xx

1983-01-26 Publication of IE46005B1 publication Critical patent/IE46005B1/en

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims 2
239000002253 acid Substances 0.000 claims abstract description 10
239000013543 active substance Substances 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 21
239000002245 particle Substances 0.000 claims description 21
239000011248 coating agent Substances 0.000 claims description 20
238000000576 coating method Methods 0.000 claims description 20
239000000825 pharmaceutical preparation Substances 0.000 claims description 17
239000008188 pellet Substances 0.000 claims description 15
238000000338 in vitro Methods 0.000 claims description 11
239000000463 material Substances 0.000 claims description 9
229920001800 Shellac Polymers 0.000 claims description 8
235000021355 Stearic acid Nutrition 0.000 claims description 8
239000002775 capsule Substances 0.000 claims description 8
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 8
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims description 8
239000004208 shellac Substances 0.000 claims description 8
229940113147 shellac Drugs 0.000 claims description 8
235000013874 shellac Nutrition 0.000 claims description 8
239000008117 stearic acid Substances 0.000 claims description 8
239000000853 adhesive Substances 0.000 claims description 7
230000001070 adhesive effect Effects 0.000 claims description 7
230000007935 neutral effect Effects 0.000 claims description 7
239000000243 solution Substances 0.000 claims description 7
239000000454 talc Substances 0.000 claims description 7
229910052623 talc Inorganic materials 0.000 claims description 7
239000011230 binding agent Substances 0.000 claims description 6
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
239000004925 Acrylic resin Substances 0.000 claims description 4
229920000178 Acrylic resin Polymers 0.000 claims description 4
239000007853 buffer solution Substances 0.000 claims description 4
239000001913 cellulose Substances 0.000 claims description 4
229920002678 cellulose Polymers 0.000 claims description 4
239000000945 filler Substances 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims 3
229920002845 Poly(methacrylic acid) Polymers 0.000 claims 2
-1 N - pyrrolidino - 4 - phenoxy - 5 - sulphamyl benzoic acid Chemical compound 0.000 claims 1
230000003111 delayed effect Effects 0.000 abstract 1
UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 description 19
229960001085 piretanide Drugs 0.000 description 18
230000000979 retarding effect Effects 0.000 description 12
208000004880 Polyuria Diseases 0.000 description 6
230000035619 diuresis Effects 0.000 description 6
206010020852 Hypertonia Diseases 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
SMYKVLBUSSNXMV-UHFFFAOYSA-K aluminum;trihydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[Al+3] SMYKVLBUSSNXMV-UHFFFAOYSA-K 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
229940024546 aluminum hydroxide gel Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011866 long-term treatment Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920001059 synthetic polymer Polymers 0.000 description 2
238000011282 treatment Methods 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001174 ascending effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000003925 fat Substances 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61P7/10—Antioedematous agents; Diuretics

Landscapes

Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Hematology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IE2474/77A 1976-12-07 1977-12-06 Preparations of 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoic acid and process for their manufacture IE46005B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762655331 DE2655331A1 (de)	1976-12-07	1976-12-07	Zubereitungsformen von 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoesaeure und verfahren zu ihrer herstellung

Publications (2)

Publication Number	Publication Date
IE46005L IE46005L (en)	1978-06-07
IE46005B1 true IE46005B1 (en)	1983-01-26

Family

ID=5994862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2474/77A IE46005B1 (en)	1976-12-07	1977-12-06	Preparations of 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoic acid and process for their manufacture

Country Status (15)

Country	Link
JP (1)	JPS5372815A (fr)
AT (1)	AT355216B (fr)
AU (1)	AU513409B2 (fr)
BE (1)	BE861608A (fr)
DE (1)	DE2655331A1 (fr)
DK (1)	DK542877A (fr)
ES (1)	ES464642A1 (fr)
FR (1)	FR2373280A1 (fr)
GB (1)	GB1569018A (fr)
IE (1)	IE46005B1 (fr)
IL (1)	IL53539A0 (fr)
NL (1)	NL7713392A (fr)
NZ (1)	NZ185855A (fr)
PT (1)	PT67370B (fr)
ZA (1)	ZA777204B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0243891B1 (fr) *	1986-04-29	1991-08-14	Hoechst-Roussel Pharmaceuticals Incorporated	Structure stratifiée pour administrer un produit chimique avec distribution contrôlée
SE460947B (sv) *	1986-08-26	1989-12-11	Lejus Medical Ab	En multiple-unit-dos komposition av l-dopa
DK0812320T3 (da) *	1995-02-22	2003-04-14	Aventis Pharma Ltd	Amorft piretanid, polymorfe former deraf, fremgangsmåde til fremstilling deraf og deres anvendelse

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE33874B1 (en) *	1968-12-24	1974-11-27	Leo Pharm Prod Ltd	New sulphamyl-benzoic acid derivatives

1976
- 1976-12-07 DE DE19762655331 patent/DE2655331A1/de active Pending
1977
- 1977-12-01 ES ES464642A patent/ES464642A1/es not_active Expired
- 1977-12-02 NL NL7713392A patent/NL7713392A/xx not_active Application Discontinuation
- 1977-12-05 NZ NZ185855A patent/NZ185855A/xx unknown
- 1977-12-05 ZA ZA00777204A patent/ZA777204B/xx unknown
- 1977-12-05 IL IL53539A patent/IL53539A0/xx unknown
- 1977-12-06 IE IE2474/77A patent/IE46005B1/en unknown
- 1977-12-06 AU AU31274/77A patent/AU513409B2/en not_active Expired
- 1977-12-06 PT PT67370A patent/PT67370B/pt unknown
- 1977-12-06 DK DK542877A patent/DK542877A/da not_active Application Discontinuation
- 1977-12-06 AT AT873777A patent/AT355216B/de not_active IP Right Cessation
- 1977-12-07 GB GB50915/77A patent/GB1569018A/en not_active Expired
- 1977-12-07 JP JP14619077A patent/JPS5372815A/ja active Pending
- 1977-12-07 BE BE183258A patent/BE861608A/fr unknown
- 1977-12-07 FR FR7736876A patent/FR2373280A1/fr active Granted

Also Published As

Publication number	Publication date
PT67370B (de)	1979-09-20
FR2373280B1 (fr)	1980-06-20
BE861608A (fr)	1978-06-07
PT67370A (de)	1978-01-01
AU3127477A (en)	1979-06-14
IE46005L (en)	1978-06-07
DK542877A (da)	1978-06-08
ES464642A1 (es)	1978-09-01
NL7713392A (nl)	1978-06-09
AU513409B2 (en)	1980-11-27
JPS5372815A (en)	1978-06-28
GB1569018A (en)	1980-06-11
ATA873777A (de)	1979-07-15
IL53539A0 (en)	1978-03-10
FR2373280A1 (fr)	1978-07-07
AT355216B (de)	1980-02-25
ZA777204B (en)	1978-10-25
NZ185855A (en)	1979-10-25
DE2655331A1 (de)	1978-06-08

Publication	Publication Date	Title
US4083949A (en)	1978-04-11	New oral form of medicament and a method for producing it
US3773920A (en)	1973-11-20	Sustained release medicinal composition
US5370880A (en)	1994-12-06	Pharmaceutical formulations containing acrivastine
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CA2281420C (fr)	2008-11-18	Preparation de granules actifs sur le plan pharmaceutique
JP2535339B2 (ja)	1996-09-18	活性物質の制御速度制御用装置
US4533540A (en)	1985-08-06	Nitroglycerin-containing polymeric matrix for sustained release on topical application
RU2127587C1 (ru)	1999-03-20	Устойчивые лекарственные формы с регулируемым выделением, имеющие акриловые полимерные покрытия, (варианты) и способ их получения
US4721619A (en)	1988-01-26	Controlled absorption diltiazen pharmaceutical formulation
US5275825A (en)	1994-01-04	Compressed-molded preparations
US4806361A (en)	1989-02-21	Medicaments in sustained release unit dose form
AU592731B2 (en)	1990-01-18	Nitrofurantoin dosage form
US20010004458A1 (en)	2001-06-21	Rapidly disintegrating pellets
JPS6323814A (ja)	1988-02-01	経口投与形体の徐放性医薬組成物
JPH06503311A (ja)	1994-04-14	薬理学的に活性なイオン化可能物質を含有する新規な医薬製剤およびその製造法
CA1261268A (fr)	1989-09-26	Preparation de theophylline a liberation continue
GB1593062A (en)	1981-07-15	Coatings
JPH0764725B2 (ja)	1995-07-12	徐放性錠剤およびその製造方法
KR890006240A (ko)	1989-06-12	조절흡수 딜티아젬 제제
IE46005B1 (en)	1983-01-26	Preparations of 3-n-pyrrolidino-4-phenoxy-5-sulfamyl-benzoic acid and process for their manufacture
US5230901A (en)	1993-07-27	Sustained release tablet of a mixture of alginates and polyacrylates
US5968552A (en)	1999-10-19	Diltiazem hydrochloride formulation
JPH01313431A (ja)	1989-12-18	ジルチアゼム・マイクロビーズ、その製法および徐放性医薬組成物
CN102970980A (zh)	2013-03-13	控制释放的左乙拉西坦配方
CA2006184C (fr)	1999-11-23	Compose a liberation prolongee a base de trimebutine et procede de preparation