EE03025B1 - Immunomoduleeriva toimega N,N'-diatsetüültsüstiini orgaanilised soolad, nende valmistamine ja kasutamine - Google Patents

Immunomoduleeriva toimega N,N'-diatsetüültsüstiini orgaanilised soolad, nende valmistamine ja kasutamine

Info

Publication number
EE03025B1
EE03025B1 EE9400378A EE9400378A EE03025B1 EE 03025 B1 EE03025 B1 EE 03025B1 EE 9400378 A EE9400378 A EE 9400378A EE 9400378 A EE9400378 A EE 9400378A EE 03025 B1 EE03025 B1 EE 03025B1
Authority
EE
Estonia
Prior art keywords
diacetylcystine
immunomodulatory
preparation
organic salts
salts
Prior art date
Application number
EE9400378A
Other languages
English (en)
Inventor
Andersson Carl-Magnus
Bergstrand H�kan
Jakupovic Edib
Josefsson Bo-G�ran
Lindvall Magnus
S�rnstrand Bengt
Teneberg Eric
Original Assignee
Astra Aktiebolag
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.)
Filing date
Publication date
Application filed by Astra Aktiebolag filed Critical Astra Aktiebolag
Publication of EE03025B1 publication Critical patent/EE03025B1/et

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
EE9400378A 1991-11-29 1994-11-17 Immunomoduleeriva toimega N,N'-diatsetüültsüstiini orgaanilised soolad, nende valmistamine ja kasutamine EE03025B1 (et)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE9103572A SE9103572D0 (sv) 1991-11-29 1991-11-29 Organic salts of n,n'-diacetyl cystine

Publications (1)

Publication Number Publication Date
EE03025B1 true EE03025B1 (et) 1997-08-15

Family

ID=20384494

Family Applications (1)

Application Number Title Priority Date Filing Date
EE9400378A EE03025B1 (et) 1991-11-29 1994-11-17 Immunomoduleeriva toimega N,N'-diatsetüültsüstiini orgaanilised soolad, nende valmistamine ja kasutamine

Country Status (38)

Country Link
US (5) US5385904A (et)
EP (1) EP0621862B1 (et)
JP (1) JP3302018B2 (et)
KR (1) KR100256185B1 (et)
CN (1) CN1039586C (et)
AP (1) AP350A (et)
AT (1) ATE141913T1 (et)
AU (1) AU657827B2 (et)
CA (1) CA2123516A1 (et)
CZ (1) CZ282085B6 (et)
DE (1) DE69213256T2 (et)
DK (1) DK0621862T3 (et)
DZ (1) DZ1637A1 (et)
EE (1) EE03025B1 (et)
ES (1) ES2090713T3 (et)
FI (1) FI942504A0 (et)
GR (1) GR3021546T3 (et)
HK (1) HK62297A (et)
HR (1) HRP921322B1 (et)
HU (1) HU215390B (et)
IL (1) IL103778A (et)
IS (1) IS1645B (et)
LV (1) LV11949B (et)
MA (1) MA22716A1 (et)
MX (1) MX9206851A (et)
MY (1) MY110523A (et)
NO (1) NO301325B1 (et)
NZ (1) NZ245077A (et)
PL (2) PL170787B1 (et)
RU (1) RU2135468C1 (et)
SE (1) SE9103572D0 (et)
SG (1) SG73962A1 (et)
SI (1) SI9200351A (et)
SK (1) SK281697B6 (et)
TN (1) TNSN92108A1 (et)
WO (1) WO1993011104A1 (et)
YU (1) YU48594B (et)
ZA (1) ZA928739B (et)

Families Citing this family (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3865463A (en) * 1973-11-12 1975-02-11 Busch & Co Inc Ag Electrical adapter plug
DE69214467T3 (de) * 1991-01-10 2000-09-28 Transcend Therapeutics Inc Verwendung von L-2-oxo Thiazolidin-4-carboxylat zur Behandlung von Atemnotsyndrom
US5747459A (en) * 1991-02-04 1998-05-05 Nestec, Ltd. Method for insuring adequate intracellular glutathione in tissue
US5430045A (en) * 1992-04-23 1995-07-04 Free Radical Sciences, Inc. Method of reducing or preventing bone marrow hypoplasia
US5447712A (en) * 1993-12-09 1995-09-05 Free Radical Sciences Method of reducing cyclophosphamide induced hemorrhagic cystitis
SE9500897D0 (sv) * 1995-03-14 1995-03-14 Astra Ab The pharmacological use of certain cystine derivatives
SE9602262D0 (sv) * 1996-06-06 1996-06-06 Astra Ab New use of derivatives of cystine
SE9602416D0 (sv) * 1996-06-18 1996-06-18 Astra Ab New forms of an organic salt of N'N-diacetylcystine
US6017959A (en) * 1996-06-18 2000-01-25 Astra Aktiebolag Forms of organic salts of N,N'-diacetylcystine
AR007398A1 (es) * 1996-06-18 1999-10-27 Astrazeneca Ab Proceso para preparar sales inorganicas de n-n'-diacetilcistina
CN1059907C (zh) * 1997-05-23 2000-12-27 中国石油化工集团公司巴陵石化岳阳石油化工总厂 一种含共轭二烯轻聚合物的选择氢化方法
US6197749B1 (en) * 1997-10-29 2001-03-06 Ajinomoto Co., Inc. Method of suppressing immune responses by reducing intracellular content of glutathione in macrophages and monocytes
US20030203006A1 (en) * 1997-10-29 2003-10-30 Ajinomoto Co. Inc. Immunomodulator
SE9800932D0 (sv) 1998-03-20 1998-03-20 Astra Ab New compunds
EP1004302A3 (en) * 1998-10-29 2003-06-04 Ajinomoto Co., Inc. Immunomodulator
SE9900438D0 (sv) * 1999-02-10 1999-02-10 Astra Ab The pharmacological use of certian cystine derivatives
US9006175B2 (en) 1999-06-29 2015-04-14 Mannkind Corporation Potentiation of glucose elimination
SE518784C2 (sv) * 2000-12-27 2002-11-19 Nactilus Ab "N-Acetyl-L-cystein med kompositioner för behandling av neoplasier"
KR20040021589A (ko) * 2001-03-13 2004-03-10 아지노모토 가부시키가이샤 화장품 또는 피부 외용제
ES2425392T3 (es) 2002-03-20 2013-10-15 Mannkind Corporation Cartucho para un aparato de inhalación
ATE486064T1 (de) 2004-08-20 2010-11-15 Mannkind Corp Katalyse der diketopiperazinsynthese
PL1791542T3 (pl) 2004-08-23 2015-11-30 Mannkind Corp Sole diketopiperazyny do dostarczania leków
AU2006290870B2 (en) 2005-09-14 2013-02-28 Mannkind Corporation Method of drug formulation based on increasing the affinity of active agents for crystalline microparticle surfaces
EP2497484A3 (en) 2006-02-22 2012-11-07 MannKind Corporation A method for improving the pharmaceutic properties of microparticles comprising diketopiperazine and an active agent
US8438729B2 (en) * 2006-03-09 2013-05-14 Canon Kabushiki Kaisha Method of producing liquid discharge head
DK2570147T3 (da) 2008-06-13 2018-01-29 Mannkind Corp Tørpulverinhalator og system til lægemiddelindgivelse
US8485180B2 (en) 2008-06-13 2013-07-16 Mannkind Corporation Dry powder drug delivery system
KR101628410B1 (ko) * 2008-06-20 2016-06-08 맨카인드 코포레이션 흡입 활동에 관한 실시간 프로파일링을 위한 대화형 장치 및 방법
TWI532497B (zh) 2008-08-11 2016-05-11 曼凱公司 超快起作用胰島素之用途
US8314106B2 (en) 2008-12-29 2012-11-20 Mannkind Corporation Substituted diketopiperazine analogs for use as drug delivery agents
CA2754595C (en) 2009-03-11 2017-06-27 Mannkind Corporation Apparatus, system and method for measuring resistance of an inhaler
US8734845B2 (en) 2009-06-12 2014-05-27 Mannkind Corporation Diketopiperazine microparticles with defined specific surface areas
CA2778698A1 (en) 2009-11-03 2011-05-12 Mannkind Corporation An apparatus and method for simulating inhalation efforts
RU2531455C2 (ru) 2010-06-21 2014-10-20 Маннкайнд Корпорейшн Системы и способы доставки сухих порошковых лекарств
MY180552A (en) 2011-04-01 2020-12-02 Mannkind Corp Blister package for pharmaceutical cartridges
WO2012174472A1 (en) 2011-06-17 2012-12-20 Mannkind Corporation High capacity diketopiperazine microparticles
WO2013063160A1 (en) 2011-10-24 2013-05-02 Mannkind Corporation Methods and compositions for treating pain
CN102491926B (zh) * 2011-12-15 2013-09-25 青岛市药品检验所 一种硫普罗宁二硫化物的制备和纯化方法
CA2878457C (en) 2012-07-12 2021-01-19 Mannkind Corporation Dry powder drug delivery systems and methods
WO2014066856A1 (en) 2012-10-26 2014-05-01 Mannkind Corporation Inhalable influenza vaccine compositions and methods
BR112015023168B1 (pt) 2013-03-15 2021-08-10 Mannkind Corporation Composição de 3,6-bis(n-fumaril-4-aminobutil)-2,5-dicetopiperazina cristalina, método de produção de partículas de 3,6-bis(n-fumaril-4-aminobutil)-2,5-dicetopiperazina e uso de uma composição de dicetopiperazina cristalina
CN114848614A (zh) 2013-07-18 2022-08-05 曼金德公司 热稳定性干粉药物组合物和方法
CA2920488C (en) 2013-08-05 2022-04-26 Mannkind Corporation Insufflation apparatus and methods
US10307464B2 (en) 2014-03-28 2019-06-04 Mannkind Corporation Use of ultrarapid acting insulin
US10561806B2 (en) 2014-10-02 2020-02-18 Mannkind Corporation Mouthpiece cover for an inhaler
US20230157939A1 (en) * 2020-04-28 2023-05-25 Conopco, Inc., D/B/A Unilever Personal care compositions with enhanced solubility actives
EP4216939A1 (en) * 2020-09-28 2023-08-02 Georgia Tech Research Corporation Use of cystine and derivatives thereof as anti-thrombotic and thrombolytic agents

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB592631A (en) * 1945-04-04 1947-09-24 Du Pont Cysteine and cystine
GB954268A (en) 1962-02-26 1964-04-02 Mead Johnson & Co Decongestant compositions comprising n-acylated sulphydryl compounds
FR8205M (et) * 1968-12-20 1970-09-14
US3647834A (en) * 1969-08-11 1972-03-07 Mead Johnson & Co Zinc mercaptide n-acetylcysteine carboxylate salts
US3878305A (en) 1972-05-25 1975-04-15 Procter & Gamble Fortification of foodstuffs with n-acyl derivatives of sulphur-containing l-amino acids
US3952115A (en) * 1975-04-02 1976-04-20 The Procter & Gamble Company Fortification of foodstuffs with N-acyl derivatives of sulfur-containing L-amino acid esters
US4141734A (en) * 1975-09-11 1979-02-27 Ciba-Geiby Ag Photographic developing process
US4093739A (en) * 1977-06-15 1978-06-06 Mead Johnson & Company Mercaptoacylamidobenzoyl glycine and mucolytic process
JPS6011888B2 (ja) * 1978-10-11 1985-03-28 参天製薬株式会社 リウマチ疾患治療薬
JPS56155298A (en) 1980-05-02 1981-12-01 Tanabe Seiyaku Co Shampoo composition
GB2097256B (en) * 1981-04-02 1985-05-30 Morelle Jean V Compositions containing n-butyryl alphaaminoacids
FR2503151A1 (fr) * 1981-04-02 1982-10-08 Morelle Jean Butyryminoacides soufres. mode de preparation. emploi comme element keratogenique chez l'homme et l'animal et comme agent de fertilisation chez les vegetaux
JPS58164566A (ja) * 1982-03-09 1983-09-29 Kenji Okawa シスチン類の製造法
US4724239A (en) * 1985-09-16 1988-02-09 Morgan Lee R Method of treating chemical ulcers with N,N'-diacetylcystine, N-acetyl homocysteine and N-acetyl cysteine
US4827016A (en) * 1985-09-16 1989-05-02 Morgan Lee R Method and compounds for reducing dermal inflammations
US4708965A (en) 1985-09-16 1987-11-24 Morgan Lee R Method of treating herpes virus infections with N,N'-diacetylcystine and derivatives
JPH0660157B2 (ja) * 1985-11-20 1994-08-10 三井東圧化学株式会社 システインからシスチンを製造する方法
JPS62195356A (ja) * 1986-02-20 1987-08-28 Seiwa Kasei:Kk シスチン誘導体及びその塩
AT402931B (de) * 1986-11-07 1997-09-25 Pharmacia Gmbh Verfahren zur herstellung von neuen cystinverbindungen und derenverwendung
SE8704542D0 (sv) * 1987-11-19 1987-11-19 Draco Ab New derivatives of cysteine
IL98310A (en) * 1990-06-08 1996-08-04 Astra Ab Medicinal preparations containing a history of cystine
TW221376B (et) * 1990-06-28 1994-03-01 Astra Ab
GB9111885D0 (en) * 1991-06-03 1991-07-24 Erba Carlo Spa Nerve growth factor for use in the prevention and treatment of viral infections

Also Published As

Publication number Publication date
AP350A (en) 1994-08-09
DK0621862T3 (da) 1996-09-16
US5804582A (en) 1998-09-08
CZ129794A3 (en) 1995-01-18
HRP921322B1 (en) 1998-12-31
CN1073683A (zh) 1993-06-30
SG73962A1 (en) 2000-07-18
SE9103572D0 (sv) 1991-11-29
HU9401473D0 (en) 1994-08-29
IL103778A (en) 1997-08-14
MA22716A1 (fr) 1993-07-01
CA2123516A1 (en) 1993-06-10
AU657827B2 (en) 1995-03-23
IL103778A0 (en) 1993-04-04
AU3099692A (en) 1993-06-28
AP9200448A0 (en) 1993-01-31
US5693858A (en) 1997-12-02
KR100256185B1 (ko) 2000-05-15
TNSN92108A1 (fr) 1993-06-08
EP0621862A1 (en) 1994-11-02
US5385904A (en) 1995-01-31
NZ245077A (en) 1995-04-27
NO941968L (no) 1994-05-26
MY110523A (en) 1998-07-31
RU2135468C1 (ru) 1999-08-27
US5824681A (en) 1998-10-20
HUT70851A (en) 1995-11-28
CN1039586C (zh) 1998-08-26
SK63294A3 (en) 1995-02-08
HU215390B (hu) 1998-12-28
SK281697B6 (sk) 2001-06-11
DZ1637A1 (fr) 2002-02-17
MX9206851A (es) 1993-05-01
WO1993011104A1 (en) 1993-06-10
DE69213256T2 (de) 1997-01-23
EP0621862B1 (en) 1996-08-28
PL171336B1 (en) 1997-04-30
CZ282085B6 (cs) 1997-05-14
SI9200351A (en) 1993-06-30
US5650538A (en) 1997-07-22
ES2090713T3 (es) 1996-10-16
JP3302018B2 (ja) 2002-07-15
PL170787B1 (en) 1997-01-31
LV11949A (lv) 1998-01-20
IS3949A (is) 1993-05-30
DE69213256D1 (de) 1996-10-02
ZA928739B (en) 1993-06-09
GR3021546T3 (en) 1997-02-28
FI942504A (fi) 1994-05-27
FI942504A0 (fi) 1994-05-27
JPH07501539A (ja) 1995-02-16
HRP921322A2 (en) 1996-10-31
HK62297A (en) 1997-05-16
NO941968D0 (no) 1994-05-26
LV11949B (en) 1998-07-20
IS1645B (is) 1997-03-25
YU99092A (sh) 1995-12-04
YU48594B (sh) 1998-12-23
ATE141913T1 (de) 1996-09-15
NO301325B1 (no) 1997-10-13

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