OA11169A - Pharmaceutical compositions of tizoxanide and nitazoxanide - Google Patents

Pharmaceutical compositions of tizoxanide and nitazoxanide Download PDF

Info

Publication number: OA11169A
Authority: OA; OAPI
Prior art keywords: acid; composition; formula; compound; particles
Prior art date: 1997-05-07

Application number

OA9900239A

Other languages

English (en)

Inventor

Jean-Francois Rossignol

Original Assignee

Romark Lab Lc

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.)

1997-05-07

Filing date

1999-10-29

Publication date

2003-04-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27420362&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA11169(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-05-07 Priority claimed from US08/852,447 external-priority patent/US5968961A/en

1997-07-03 Priority claimed from US08/887,810 external-priority patent/US5856348A/en

1997-07-03 Priority claimed from US08/887,809 external-priority patent/US5965590A/en

1999-10-29 Application filed by Romark Lab Lc filed Critical Romark Lab Lc

2003-04-25 Publication of OA11169A publication Critical patent/OA11169A/en

Links

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FDTZUTSGGSRHQF-UHFFFAOYSA-N Desacetyl-nitazoxanide Chemical group OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 FDTZUTSGGSRHQF-UHFFFAOYSA-N 0.000 title description 19
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VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
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238000012986 modification Methods 0.000 description 1
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231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
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244000052769 pathogen Species 0.000 description 1
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WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
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230000001105 regulatory effect Effects 0.000 description 1
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230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002356 single layer Substances 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 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
229940080313 sodium starch Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000011301 standard therapy Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
229960004306 sulfadiazine Drugs 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
210000000059 tachyzoite Anatomy 0.000 description 1
239000000454 talc Substances 0.000 description 1
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239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000002568 urticarial effect Effects 0.000 description 1
238000005303 weighing Methods 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- A61P33/12—Schistosomicides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Immunology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Virology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

OA9900239A 1997-05-07 1999-10-29 Pharmaceutical compositions of tizoxanide and nitazoxanide OA11169A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/852,447 US5968961A (en)	1997-05-07	1997-05-07	Pharmaceutical compositions of tizoxanide and nitazoxanide
US08/887,810 US5856348A (en)	1994-09-08	1997-07-03	Method for treatment of trematodes with pharmaceutical compositions of tizoxanide and nitazoxanide
US08/887,809 US5965590A (en)	1994-09-08	1997-07-03	Method for treatment of opportunistic infections with pharmaceutical compositions of tizoxanide and nitazoxanide

Publications (1)

Publication Number	Publication Date
OA11169A true OA11169A (en)	2003-04-25

Family

ID=27420362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900239A OA11169A (en)	1997-05-07	1999-10-29	Pharmaceutical compositions of tizoxanide and nitazoxanide

Country Status (34)

Country	Link
EP (2)	EP1222921B1 (no)
JP (1)	JP3739802B2 (no)
KR (2)	KR100576646B1 (no)
CN (2)	CN100515420C (no)
AP (1)	AP1103A (no)
AR (1)	AR057242A2 (no)
AT (2)	ATE281166T1 (no)
AU (1)	AU740022B2 (no)
BG (2)	BG109365A (no)
BR (1)	BR9808722A (no)
CA (2)	CA2288003C (no)
CZ (2)	CZ298270B6 (no)
DE (2)	DE69809928T2 (no)
DK (2)	DK1005342T3 (no)
EA (2)	EA002908B1 (no)
EE (1)	EE04870B1 (no)
ES (2)	ES2232687T3 (no)
GE (1)	GEP20032970B (no)
HU (1)	HU229641B1 (no)
IL (2)	IL132516A (no)
IS (1)	IS2087B (no)
LV (1)	LV12492B (no)
ME (1)	ME00530B (no)
NO (2)	NO313983B1 (no)
NZ (2)	NZ513881A (no)
OA (1)	OA11169A (no)
PL (1)	PL193275B1 (no)
PT (2)	PT1005342E (no)
RO (1)	RO120605B1 (no)
SI (1)	SI20149B (no)
SK (2)	SK283947B6 (no)
TR (1)	TR199902733T2 (no)
UA (2)	UA57079C2 (no)
WO (1)	WO1998050035A1 (no)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2467321A1 (en)	2004-05-14	2005-11-14	Paul J. Santerre	Polymeric coupling agents and pharmaceutically-active polymers made therefrom
MX2008008723A (es) *	2006-01-09	2008-09-26	Romark Lab Lc	Tratamiento de la hepatitis viral.
MX381895B (es) *	2009-02-13	2025-03-13	Romark Laboratories Lc	Formulaciones farmaceuticas de liberacion controlada de nitazoxanida.
CN105853415A (zh)	2009-05-12	2016-08-17	罗马克实验室有限公司	卤代烷基杂芳基苯甲酰胺化合物
BRPI1014322A2 (pt)	2009-06-26	2015-08-25	Romark Lab Lc	Método para tratar infecção, e para interromper ou evitar a produção de partículas virais infecciosas, combinação, e, composição farmacêutica.
US9498441B2 (en)	2012-01-27	2016-11-22	Siegfried Rhein S.A. De C.V.	Nitazoxadine composition and process to prepare same
JP6633092B2 (ja) *	2014-11-11	2020-01-22	ロマークラボラトリーズ，リミティドカンパニー	チゾキサニド、その類似体又は塩のプロドラッグを用いる組成物及び治療方法
EP3740494A4 (en)	2018-02-02	2021-11-03	Ripple Therapeutics Corporation	GLASS FORMULATIONS WITH STEROID DIMERS AND USES THEREOF
WO2019241376A1 (en)	2018-06-14	2019-12-19	The Trustees Of Columbia University In The City Of New York	Treatment of cognitive disorders using nitazoxanide (ntz), nitazoxanide (ntz) analogs, and metabolites thereof
WO2020154815A1 (en)	2019-02-01	2020-08-06	Ripple Therapeutics Corporation	Crystalline forms of dexamethasone dimers and uses thereof
US12509469B2 (en)	2019-08-07	2025-12-30	Ripple Therapeutics Corporation	Compositions and methods for the treatment of pain and dependence disorders
CA3176134A1 (en)	2020-05-01	2021-11-04	Ripple Therapeutics Corporation	Heterodimer compositions and methods for the treatment of ocular disorders
WO2022130406A1 (en) *	2020-12-15	2022-06-23	Cipla Limited	Inhalation composition of nitazoxanide or its derivatives for use in coronavirus disease

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1437800A (en) *	1973-08-08	1976-06-03	Phavic Sprl	Derivatives of 2-benzamido-5-nitro-thiazoles
US4315018A (en) *	1978-12-07	1982-02-09	Rossignol Jean F	Specific parasiticidal use of 2-benzamido-5-nitro-thiazole derivatives
US5387598A (en) *	1994-04-13	1995-02-07	Rossignol; Jean-Francois	Composition and galenic formulation suitable for combatting affections of the lower abdomen
US5578621A (en) *	1994-09-08	1996-11-26	Romark Lab Lc	Benzamide derivatives

1998
- 1998-05-06 SI SI9820037A patent/SI20149B/sl not_active IP Right Cessation
- 1998-05-06 KR KR1020037011334A patent/KR100576646B1/ko not_active Expired - Fee Related
- 1998-05-06 HU HU0003330A patent/HU229641B1/hu not_active IP Right Cessation
- 1998-05-06 ES ES02002887T patent/ES2232687T3/es not_active Expired - Lifetime
- 1998-05-06 EP EP02002887A patent/EP1222921B1/en not_active Expired - Lifetime
- 1998-05-06 NZ NZ513881A patent/NZ513881A/xx not_active IP Right Cessation
- 1998-05-06 EA EA199901012A patent/EA002908B1/ru not_active IP Right Cessation
- 1998-05-06 NZ NZ500149A patent/NZ500149A/en not_active IP Right Cessation
- 1998-05-06 SK SK708-2003A patent/SK283947B6/sk unknown
- 1998-05-06 AU AU72895/98A patent/AU740022B2/en not_active Ceased
- 1998-05-06 CN CNB2004100459536A patent/CN100515420C/zh not_active Expired - Fee Related
- 1998-05-06 GE GEAP19985109A patent/GEP20032970B/en unknown
- 1998-05-06 SK SK1511-99A patent/SK283946B6/sk unknown
- 1998-05-06 AP APAP/P/1999/001675A patent/AP1103A/en active
- 1998-05-06 AT AT02002887T patent/ATE281166T1/de active
- 1998-05-06 DK DK98920285T patent/DK1005342T3/da active
- 1998-05-06 CN CNB988049007A patent/CN1158074C/zh not_active Expired - Fee Related
- 1998-05-06 ME MEP-2008-877A patent/ME00530B/me unknown
- 1998-05-06 WO PCT/US1998/009229 patent/WO1998050035A1/en not_active Ceased
- 1998-05-06 IL IL13251698A patent/IL132516A/xx not_active IP Right Cessation
- 1998-05-06 JP JP54843798A patent/JP3739802B2/ja not_active Expired - Fee Related
- 1998-05-06 CA CA002288003A patent/CA2288003C/en not_active Expired - Fee Related
- 1998-05-06 EE EEP199900578A patent/EE04870B1/xx unknown
- 1998-05-06 CA CA002418634A patent/CA2418634C/en not_active Expired - Fee Related
- 1998-05-06 AT AT98920285T patent/ATE228839T1/de active
- 1998-05-06 PT PT98920285T patent/PT1005342E/pt unknown
- 1998-05-06 EA EA200100956A patent/EA002920B1/ru not_active IP Right Cessation
- 1998-05-06 CZ CZ20060366A patent/CZ298270B6/cs not_active IP Right Cessation
- 1998-05-06 RO RO99-01166A patent/RO120605B1/ro unknown
- 1998-05-06 DE DE69809928T patent/DE69809928T2/de not_active Expired - Lifetime
- 1998-05-06 KR KR10-1999-7009930A patent/KR100426657B1/ko not_active Expired - Lifetime
- 1998-05-06 EP EP98920285A patent/EP1005342B1/en not_active Expired - Lifetime
- 1998-05-06 PT PT02002887T patent/PT1222921E/pt unknown
- 1998-05-06 TR TR1999/02733T patent/TR199902733T2/xx unknown
- 1998-05-06 BR BR9808722-3A patent/BR9808722A/pt not_active IP Right Cessation
- 1998-05-06 ES ES98920285T patent/ES2150404T3/es not_active Expired - Lifetime
- 1998-05-06 DE DE69827417T patent/DE69827417T2/de not_active Expired - Lifetime
- 1998-05-06 PL PL336805A patent/PL193275B1/pl not_active IP Right Cessation
- 1998-05-06 DK DK02002887T patent/DK1222921T3/da active
- 1998-05-06 IL IL15579998A patent/IL155799A/en not_active IP Right Cessation
- 1998-05-06 CZ CZ0391199A patent/CZ298269B6/cs not_active IP Right Cessation
- 1998-06-05 UA UA99126626A patent/UA57079C2/uk unknown
- 1998-12-06 BG BG109365A patent/BG109365A/en unknown
1999
- 1999-10-19 IS IS5223A patent/IS2087B/is unknown
- 1999-10-29 OA OA9900239A patent/OA11169A/en unknown
- 1999-11-04 NO NO19995406A patent/NO313983B1/no not_active IP Right Cessation
- 1999-12-01 LV LVP-99-170A patent/LV12492B/en unknown
- 1999-12-06 BG BG103958A patent/BG64973B1/bg unknown
2002
- 2002-04-18 NO NO20021832A patent/NO335781B1/no not_active IP Right Cessation
2003
- 2003-04-04 UA UA2003042974A patent/UA74388C2/uk unknown
2006
- 2006-12-14 AR ARP060105534A patent/AR057242A2/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69809928T2 (de)	2003-04-24
CN1158074C (zh)	2004-07-21
IS2087B (is)	2006-03-15
NO995406D0 (no)	1999-11-04
NO995406L (no)	2000-01-04
SI20149B (en)	2001-08-31
EP1222921A1 (en)	2002-07-17
EA002920B1 (ru)	2002-10-31
RO120605B1 (ro)	2006-05-30
CA2288003A1 (en)	1998-11-12
DE69827417D1 (de)	2004-12-09
DE69809928D1 (de)	2003-01-16
NO20021832L (no)	2000-01-04
PL193275B1 (pl)	2007-01-31
BR9808722A (pt)	2000-07-11
DE69827417T2 (de)	2005-10-27
NO335781B1 (no)	2015-02-16
ATE228839T1 (de)	2002-12-15
DK1222921T3 (da)	2005-03-07
ES2232687T3 (es)	2005-06-01
ME00530B (me)	2011-10-10
AU7289598A (en)	1998-11-27
CN1255060A (zh)	2000-05-31
EA002908B1 (ru)	2002-10-31
EP1005342A4 (en)	2001-02-07
IS5223A (is)	1999-10-19
CZ298269B6 (cs)	2007-08-08
JP2001503067A (ja)	2001-03-06
UA57079C2 (uk)	2003-06-16
ATE281166T1 (de)	2004-11-15
JP3739802B2 (ja)	2006-01-25
EA199901012A1 (ru)	2000-08-28
SI20149A (sl)	2000-08-31
HK1025907A1 (en)	2000-12-01
KR20010020322A (ko)	2001-03-15
EE9900578A (et)	2000-08-15
NO20021832D0 (no)	2002-04-18
KR100426657B1 (ko)	2004-04-13
CN100515420C (zh)	2009-07-22
TR199902733T2 (xx)	2000-03-21
EP1005342B1 (en)	2002-12-04
SK283946B6 (sk)	2004-05-04
IL155799A (en)	2004-08-31
LV12492B (en)	2001-01-20
CZ298270B6 (cs)	2007-08-08
CA2288003C (en)	2003-10-21
HUP0003330A3 (en)	2002-10-28
WO1998050035A1 (en)	1998-11-12
KR20040004544A (ko)	2004-01-13
SK151199A3 (en)	2000-07-11
EP1222921B1 (en)	2004-11-03
CZ391199A3 (cs)	2000-07-12
HUP0003330A2 (hu)	2001-05-28
ES2150404T3 (es)	2003-07-01
NZ500149A (en)	2001-11-30
AR057242A2 (es)	2007-11-21
UA74388C2 (uk)	2005-12-15
PT1005342E (pt)	2003-02-28
AU740022B2 (en)	2001-10-25
BG109365A (en)	2006-08-31
CN1552322A (zh)	2004-12-08
AP9901675A0 (en)	1999-12-31
CA2418634C (en)	2004-10-26
BG64973B1 (bg)	2006-11-30
NZ513881A (en)	2002-10-25
SK283947B6 (sk)	2004-05-04
IL132516A0 (en)	2001-03-19
EP1005342A1 (en)	2000-06-07
CA2418634A1 (en)	1998-11-12
DK1005342T3 (da)	2003-03-24
LV12492A (en)	2000-06-20
PT1222921E (pt)	2005-02-28
IL132516A (en)	2003-12-10
PL336805A1 (en)	2000-07-17
EE04870B1 (et)	2007-08-15
AP1103A (en)	2002-09-04
ES2150404T1 (es)	2000-12-01
GEP20032970B (en)	2003-05-27
KR100576646B1 (ko)	2006-05-08
NO313983B1 (no)	2003-01-13
BG103958A (en)	2000-07-31
EA200100956A1 (ru)	2002-02-28
IL155799A0 (en)	2003-12-23
HU229641B1 (en)	2014-03-28

Publication	Publication Date	Title
US5965590A (en)	1999-10-12	Method for treatment of opportunistic infections with pharmaceutical compositions of tizoxanide and nitazoxanide
RS50046B (sr)	2008-11-28	Farmaceutske kompozicije tizoksanida i nitazoksanida
RS57199B1 (sr)	2018-07-31	Ekstrakti kakaa, proizvodi od kakaa i postupci za njihovu proizvodnju
AU740022B2 (en)	2001-10-25	Pharmaceutical compositions of tizoxanide and nitazoxanide
AU756451B2 (en)	2003-01-16	Pharmaceutical compositions of tizoxanide and nitazoxanide