KR840002350A - N-아세틸시스테인의 살리실산 유도체의 제조 방법 - Google Patents
N-아세틸시스테인의 살리실산 유도체의 제조 방법 Download PDFInfo
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- KR840002350A KR840002350A KR1019820005229A KR820005229A KR840002350A KR 840002350 A KR840002350 A KR 840002350A KR 1019820005229 A KR1019820005229 A KR 1019820005229A KR 820005229 A KR820005229 A KR 820005229A KR 840002350 A KR840002350 A KR 840002350A
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- South Korea
- Prior art keywords
- process according
- acid
- acetylcysteine
- organic
- salicylic acid
- Prior art date
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- 150000003872 salicylic acid derivatives Chemical class 0.000 title claims 9
- 229960004308 acetylcysteine Drugs 0.000 title claims 7
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims 10
- 150000007530 organic bases Chemical class 0.000 claims 10
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000001340 alkali metals Chemical group 0.000 claims 3
- 239000002585 base Chemical group 0.000 claims 3
- 150000007529 inorganic bases Chemical class 0.000 claims 3
- GGQJXCQBBONZFX-IWVLMIASSA-N meclocycline Chemical compound C=C([C@H]1[C@@H]2O)C3=C(Cl)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O GGQJXCQBBONZFX-IWVLMIASSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 229960003276 erythromycin Drugs 0.000 claims 2
- TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 claims 2
- 229950001028 erythromycin propionate Drugs 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- 229960000826 meclocycline Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000008196 pharmacological composition Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 238000011200 topical administration Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 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 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 229930193140 Neomycin Natural products 0.000 claims 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 230000001754 anti-pyretic effect Effects 0.000 claims 1
- 239000002221 antipyretic Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 230000000510 mucolytic effect Effects 0.000 claims 1
- 229960004927 neomycin Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000007970 thio esters Chemical class 0.000 claims 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (21)
- 다음 일반식인 N－아세틸시스테인의 살리실산 유도체.상기 일반식에서, X는 수소, 알칼리 금속류, 알칼리토 금속류, 그리고 유기 염기류의 기(基)로 이루어진 군에서 선택됨.
- 제1항에 있어서, 유기 염기가 염기성 아미노산임을 특징으로 하는 살리실산 유도체.
- 제2항에 있어서, 염기성 아미노산이 리신과 아르기닌 사이에서 선택됨을 특징으로 하는 살리실산 유도체.
- 제1항에 있어서, 유기 염기가 염기성 항생제임을 특징으로 하는 살리실산 유도체.
- 제4항에 있어서, 상기 염기성 항생제가 에리스로마이신, 프로피온일에리스로마이신, 네오마이신 및 메클로사이클린 중에서 선택됨을 특징으로 하는 살리실산 유도체.
- 제1항에 있어서, 알칼리 금속이 나트륨임을 특징으로 하는 살리실산 유도체.
- (a) 아세틸살리실산 염화물 및 아세틸살리실산의 클로로포롬산 에틸과의 혼합 무수물 중에서 선정된 아세틸살리실산의 반응성 유도체를 제조하는 단계, (b) 산수용체로 작용하는 유기 또는 무기염기의 존재하에 N－아세틸시스테인과 저온에서 반응시키는 단계, (c) 그 결과 생성된 티오에스테르를 유리시키고 이것을 수성, 알코올성 또는 케톤성 매질 내에서 대응하는 유기 또는 무기염으로 전환시키는 단계로 구성됨을 특징으로 하는 제1항의 살리실산 유도체의 제조 방법.
- 제7항에 있어서, 반응성 유도체가 아세틸살리실산의 염화물이며, 이 염화물은 상기 아세틸살리실산을 염화티오닐과 환류시켜 제조됨을 특징으로 하는 제조 방법.
- 제7항에 있어서, 반응성 유도체가 혼합 무수물이며, 이무수물은 아세틸살리실산과 클로로포름산에틸을 유기용매 중에서 저온으로 반응시킴으로써 제조됨을 특징으로 하는 제조 방법.
- 제7항에 있어서, 반응성 유도체와 ??－아세틸시스테인과의 반응이 물 중에서 알칼리 금속의 수산화를 존재하에 1°－5℃의 온도 범위에서 수행됨을 특징으로 하는 제조 방법.
- 제7항에 있어서, 알칼리 금속의 수산화물이 수산화나트륨임을 특징으로 하는 제조방법.
- 제7항에 있어서, 반응성 유도체와 N－아세틸시스테인의 반응이 에스테르성 매질 내에서 유기 염기의 존재 하에 1°－5℃의 온도 범위에서 수행됨을 특징으로 하는 제조 방법.
- 제12항에 있어서, 유기염기가 3차 아민임을 특징으로 하는 제조 방법.
- 제10항 또는 12항에 있어서, 상기 반응 생성물을 유기염기로 처리하여 아세틸 이탈 반응을 완결시키고, 이 탈아세틸화 생성물을 산가수분해시킴으로써 살리실로일티오－N－아세틸시스테인 산을 얻음을 특징으로 하는 제조 방법.
- 제7항에 있어서, 가능한 전환반응이 살리실로일티오－N－아세틸시스테인산을 유기 또는 무기염기와반응시킴으로써 수행됨을 특징으로 하는 제조 방법.
- 제15항에 있어서, 무기염기가 탄산나트륨이고 반응은 디옥산의 물의 평형 혼합물 내에서 10℃ 이상을 넘지 않는 온도에서 수행됨을 특징으로 하는 제조 방법.
- 제15항에 있어서, 유기염기가 수용액 중의 (L) 혹은 (DL)－리신이고, 반응은 메탄올과 이소프로판올의 혼합물중에서 일어남을 특징으로 하는 제조 방법.
- 제15항에 있어서, 유기 염기가 염기 에리스토마이신, 에리스토마이신 프로피온산염 및 염기 메클로사이클린으로 구성된 군 중에서 선택됨을 특징으로 하는 제조 방법.
- 활성 성분으로서 제1항의 살리실산 유도체를 함유함을 특징으로 하는 해열작용, 소염작용, 진통작용 및 점액용해 작용을 갖는 약리학적 조성물.
- 제19항에 있어서, 경구, 비경구, 직장 및 국부투여에 적합한 약리학적 조성물.
- 활성 성분으로서 제1항의 살리실산 유도체의 메클로사이클린염을 함유함을 특징으로 하는 피부 의학적 작용을 갖는 국부 투여에 적합한 형태의 약리학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25198A/81 | 1981-11-20 | ||
| IT25198/81A IT1194117B (it) | 1981-11-20 | 1981-11-20 | Derivati salicilici di n-acetilcisteina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002350A true KR840002350A (ko) | 1984-06-25 |
| KR890000618B1 KR890000618B1 (ko) | 1989-03-22 |
Family
ID=11215991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205229A KR890000618B1 (ko) | 1981-11-20 | 1982-11-19 | N-아세틸시스테인의 살리실산 유도체의 제조방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4567163A (ko) |
| EP (1) | EP0080229B1 (ko) |
| JP (1) | JPS58146560A (ko) |
| KR (1) | KR890000618B1 (ko) |
| AT (1) | ATE12102T1 (ko) |
| CA (1) | CA1202618A (ko) |
| DE (1) | DE3262569D1 (ko) |
| ES (1) | ES517540A0 (ko) |
| IT (1) | IT1194117B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU574360B2 (en) * | 1983-05-13 | 1988-07-07 | Reichert, D. | Antisnoring agent |
| IT1206515B (it) * | 1983-08-09 | 1989-04-27 | Guidotti & C Spa Labor | N-acetilcisteina ederivati 2',4's-carbossimetilcisteina ad-difluoro-4-idrossi-(1,1'-bifenil)attivita' antinfiammatoria, 3-carbossilici della mucolitica, procedimento per laloro preparazione e relative composizioni farmaceutiche. |
| IT1194474B (it) * | 1983-11-23 | 1988-09-22 | Magis Farmaceutici | Derivati della cisteina,procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
| US5637616A (en) * | 1993-06-18 | 1997-06-10 | Arcturus Pharmaceutical Corporation | Method for treating diseases mediated by proteases |
| AU7176094A (en) * | 1993-06-18 | 1995-01-17 | Arcturus Pharmaceutical Corporation | Method for treating hyperkeratosis and diseases mediated by proteases |
| WO1995034303A1 (en) * | 1994-06-13 | 1995-12-21 | Arcturus Pharmaceutical Corporation | Method for the treatment, prevention or minimization of hair loss |
| GB2320431B (en) * | 1996-12-20 | 2000-08-30 | Johnson & Johnson Medical | Compositions for the treatment of chronic wounds |
| CN103251631A (zh) * | 2008-05-13 | 2013-08-21 | 根梅迪卡治疗公司 | 用于治疗代谢性病症的水杨酸盐(酯)缀合物 |
| BRPI1013878A2 (pt) * | 2009-03-16 | 2016-04-05 | Genmedica Therapeutics Sl | método para tratar distúrbios metabólicos, e, composto |
| WO2010106083A1 (en) * | 2009-03-16 | 2010-09-23 | Genmedica Therapeutics Sl | Combination therapies for treating metabolic disorders |
| US8466197B2 (en) | 2010-12-14 | 2013-06-18 | Genmedica Therapeutics Sl | Thiocarbonates as anti-inflammatory and antioxidant compounds useful for treating metabolic disorders |
| WO2013037984A1 (en) | 2011-09-16 | 2013-03-21 | Genmedica Therapeutics Sl | Anti-inflammatory and antioxidant conjugates useful for treating metabolic disorders |
| BR112014006150A2 (pt) | 2011-09-16 | 2017-04-04 | Genmedica Therapeutics Sl | combinação farmacêutica, e, métodos para tratar doença, síndrome ou condição, e para proteger beta-células pancreáticas |
| EP3674297A1 (en) | 2013-11-08 | 2020-07-01 | Promentis Pharmaceuticals, Inc. | Substituted n-acetyl-l-cysteine derivatives and related compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4619M (ko) * | 1965-02-01 | 1966-11-28 | ||
| US4268456A (en) * | 1979-09-24 | 1981-05-19 | Ppg Industries, Inc. | Process for preparing chlorothiolformates |
-
1981
- 1981-11-20 IT IT25198/81A patent/IT1194117B/it active
-
1982
- 1982-11-12 DE DE8282201443T patent/DE3262569D1/de not_active Expired
- 1982-11-12 EP EP82201443A patent/EP0080229B1/en not_active Expired
- 1982-11-12 AT AT82201443T patent/ATE12102T1/de not_active IP Right Cessation
- 1982-11-16 CA CA000415702A patent/CA1202618A/en not_active Expired
- 1982-11-16 US US06/442,044 patent/US4567163A/en not_active Expired - Lifetime
- 1982-11-19 KR KR8205229A patent/KR890000618B1/ko not_active IP Right Cessation
- 1982-11-19 ES ES517540A patent/ES517540A0/es active Granted
- 1982-11-20 JP JP57204423A patent/JPS58146560A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8125198A0 (it) | 1981-11-20 |
| EP0080229A1 (en) | 1983-06-01 |
| IT1194117B (it) | 1988-09-14 |
| EP0080229B1 (en) | 1985-03-13 |
| JPH059424B2 (ko) | 1993-02-04 |
| JPS58146560A (ja) | 1983-09-01 |
| DE3262569D1 (en) | 1985-04-18 |
| ES8402258A1 (es) | 1984-01-16 |
| US4567163A (en) | 1986-01-28 |
| ATE12102T1 (de) | 1985-03-15 |
| ES517540A0 (es) | 1984-01-16 |
| CA1202618A (en) | 1986-04-01 |
| KR890000618B1 (ko) | 1989-03-22 |
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