LU84095A1 - Sels d'acetylcysteine,leur preparation et leur utilisation - Google Patents

Sels d'acetylcysteine,leur preparation et leur utilisation Download PDF

Info

Publication number: LU84095A1
Authority: LU; Luxembourg
Prior art keywords: acetylcysteine; amino acid; basic amino; water; salt
Prior art date: 1982-04-19

Application number

LU84095A

Other languages

English (en)

French (fr)

Inventor

Arthur Marie Deboeck

Original Assignee

Galephar

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.)

1982-04-19

Filing date

1982-04-19

Publication date

1983-12-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19729863&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LU84095(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1982-04-19 Application filed by Galephar filed Critical Galephar

1982-04-19 Priority to LU84095A priority Critical patent/LU84095A1/fr

1983-04-18 Priority to EP83200547A priority patent/EP0092287B2/de

1983-04-18 Priority to DE8383200547T priority patent/DE3370477D1/de

1983-04-18 Priority to AT83200547T priority patent/ATE26109T1/de

1983-12-16 Publication of LU84095A1 publication Critical patent/LU84095A1/fr

1987-10-07 Priority to US07/106,005 priority patent/US4847282A/en

Links

PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical class CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 title claims abstract description 49
238000002360 preparation method Methods 0.000 title claims description 9
150000001413 amino acids Chemical class 0.000 claims abstract description 37
229960004308 acetylcysteine Drugs 0.000 claims abstract description 32
239000004472 Lysine Substances 0.000 claims abstract description 9
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 9
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 6
239000004475 Arginine Substances 0.000 claims abstract description 5
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims abstract description 5
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims abstract description 5
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 5
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims abstract description 5
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 4
239000004471 Glycine Substances 0.000 claims abstract description 3
239000007795 chemical reaction product Substances 0.000 claims abstract description 3
239000003172 expectorant agent Substances 0.000 claims abstract 2
229940066491 mucolytics Drugs 0.000 claims abstract 2
150000003839 salts Chemical class 0.000 claims description 20
239000000243 solution Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 7
238000001704 evaporation Methods 0.000 claims description 7
230000008020 evaporation Effects 0.000 claims description 7
238000000926 separation method Methods 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 6
238000004108 freeze drying Methods 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
-1 amino acid salt Chemical class 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 4
PEWXENMTDDNSMK-BYPYZUCNSA-N acetyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CC(=O)OC(=O)[C@@H](N)CS PEWXENMTDDNSMK-BYPYZUCNSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
239000000729 antidote Substances 0.000 claims description 3
OCHFNTLZOZPXFE-JEDNCBNOSA-N carbonic acid;(2s)-2,6-diaminohexanoic acid Chemical group OC(O)=O.NCCCC[C@H](N)C(O)=O OCHFNTLZOZPXFE-JEDNCBNOSA-N 0.000 claims description 3
239000006185 dispersion Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
238000004090 dissolution Methods 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
241001594857 Pao Species 0.000 claims 1
231100000570 acute poisoning Toxicity 0.000 claims 1
239000007900 aqueous suspension Substances 0.000 claims 1
229960005489 paracetamol Drugs 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 abstract 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 abstract 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 abstract 1
229960003104 ornithine Drugs 0.000 abstract 1
235000001014 amino acid Nutrition 0.000 description 19
235000018977 lysine Nutrition 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000843 powder Substances 0.000 description 5
239000002585 base Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
YLCSLYZPLGQZJS-VDQHJUMDSA-N (2r)-2-acetamido-3-sulfanylpropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(=O)N[C@@H](CS)C(O)=O.NCCCC[C@H](N)C(O)=O YLCSLYZPLGQZJS-VDQHJUMDSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
235000009697 arginine Nutrition 0.000 description 3
235000014304 histidine Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000008298 dragée Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
208000012237 paracetamol poisoning Diseases 0.000 description 2
239000000829 suppository Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
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 description 1
235000019766 L-Lysine Nutrition 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
150000008535 L-arginines Chemical class 0.000 description 1
150000008545 L-lysines Chemical class 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
235000012730 carminic acid Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000000510 mucolytic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000004552 water soluble powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU84095A 1982-04-19 1982-04-19 Sels d'acetylcysteine,leur preparation et leur utilisation LU84095A1 (fr)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
LU84095A LU84095A1 (fr)	1982-04-19	1982-04-19	Sels d'acetylcysteine,leur preparation et leur utilisation
EP83200547A EP0092287B2 (de)	1982-04-19	1983-04-18	Acetylcystein-Salze, ihre Herstellung und Verwendung
DE8383200547T DE3370477D1 (en)	1982-04-19	1983-04-18	Acetylcysteine salts, their preparation and use
AT83200547T ATE26109T1 (de)	1982-04-19	1983-04-18	Acetylcystein-salze, ihre herstellung und verwendung.
US07/106,005 US4847282A (en)	1982-04-19	1987-10-07	Mucolytic acetylcysteine salts

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU84095		1982-04-19
LU84095A LU84095A1 (fr)	1982-04-19	1982-04-19	Sels d'acetylcysteine,leur preparation et leur utilisation

Publications (1)

Publication Number	Publication Date
LU84095A1 true LU84095A1 (fr)	1983-12-16

Family

ID=19729863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84095A LU84095A1 (fr)	1982-04-19	1982-04-19	Sels d'acetylcysteine,leur preparation et leur utilisation

Country Status (5)

Country	Link
US (1)	US4847282A (de)
EP (1)	EP0092287B2 (de)
AT (1)	ATE26109T1 (de)
DE (1)	DE3370477D1 (de)
LU (1)	LU84095A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE8901570D0 (sv) *	1989-05-02	1989-05-02	Draco Ab	Organic salts of cysteine derivatives
US5637616A (en) *	1993-06-18	1997-06-10	Arcturus Pharmaceutical Corporation	Method for treating diseases mediated by proteases
AU2003254429A1 (en) *	2003-08-06	2005-02-25	Galephar M/F	Advantageous combinations for inhalation of nacystelyn and bronchodilators
US20050154060A1 (en) *	2003-12-11	2005-07-14	Galephar Pharmaceutical Research, Inc.	Anti-inflamatory inhalation pharmaceutical composition
US20080107746A1 (en) *	2004-12-13	2008-05-08	Arthur Deboeck	Anti-inflamatory inhalation pharmaceutical composition
US20080175899A1 (en) *	2007-01-19	2008-07-24	Ross Mairi R	Formulation for promoting sinus health in nasal cavities

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3184505A (en) *	1962-06-18	1965-05-18	Mead Johnson & Co	Process for the n-monoacylation of cysteine

1982
- 1982-04-19 LU LU84095A patent/LU84095A1/fr unknown
1983
- 1983-04-18 DE DE8383200547T patent/DE3370477D1/de not_active Expired
- 1983-04-18 EP EP83200547A patent/EP0092287B2/de not_active Expired - Lifetime
- 1983-04-18 AT AT83200547T patent/ATE26109T1/de not_active IP Right Cessation
1987
- 1987-10-07 US US07/106,005 patent/US4847282A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0092287A2 (de)	1983-10-26
US4847282A (en)	1989-07-11
DE3370477D1 (en)	1987-04-30
EP0092287B1 (de)	1987-03-25
EP0092287B2 (de)	1994-11-23
EP0092287A3 (en)	1984-08-15
ATE26109T1 (de)	1987-04-15

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