DD146600A5 - Verfahren zur herstellung von n hoch 2-arylsulfonyl-l-argininamiden und der pharmazeutisch annehmbaren salze - Google Patents
Verfahren zur herstellung von n hoch 2-arylsulfonyl-l-argininamiden und der pharmazeutisch annehmbaren salze Download PDFInfo
- Publication number
- DD146600A5 DD146600A5 DD79215205A DD21520579A DD146600A5 DD 146600 A5 DD146600 A5 DD 146600A5 DD 79215205 A DD79215205 A DD 79215205A DD 21520579 A DD21520579 A DD 21520579A DD 146600 A5 DD146600 A5 DD 146600A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- alkyl group
- carbon atoms
- methyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000003839 salts Chemical class 0.000 title claims abstract description 15
- -1 8-quinolyl group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000005907 alkyl ester group Chemical class 0.000 claims description 3
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- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- GHBNOCBWSUHAAA-HTQZYQBOSA-N ethyl (2r,4r)-4-methylpiperidine-2-carboxylate Chemical compound CCOC(=O)[C@H]1C[C@H](C)CCN1 GHBNOCBWSUHAAA-HTQZYQBOSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 description 1
- 229950003499 fibrin Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 229940124280 l-arginine Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- ZJMLWSBTWUELPE-UHFFFAOYSA-N oxo(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C(=O)C1=CC=CC=C1 ZJMLWSBTWUELPE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- VHXJRLYFEJAIAM-UHFFFAOYSA-N quinoline-2-sulfonyl chloride Chemical compound C1=CC=CC2=NC(S(=O)(=O)Cl)=CC=C21 VHXJRLYFEJAIAM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/938,711 US4201863A (en) | 1974-11-08 | 1978-08-31 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US06/041,419 US4258192A (en) | 1977-12-16 | 1979-05-22 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD146600A5 true DD146600A5 (de) | 1981-02-18 |
Family
ID=26718116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79215205A DD146600A5 (de) | 1978-08-31 | 1979-08-27 | Verfahren zur herstellung von n hoch 2-arylsulfonyl-l-argininamiden und der pharmazeutisch annehmbaren salze |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0008746B1 (cs) |
| AU (1) | AU520342B2 (cs) |
| CA (1) | CA1135698A (cs) |
| CS (1) | CS228119B2 (cs) |
| DD (1) | DD146600A5 (cs) |
| DE (1) | DE2963539D1 (cs) |
| DK (1) | DK152495C (cs) |
| ES (1) | ES483767A1 (cs) |
| FI (1) | FI66183C (cs) |
| GR (1) | GR64905B (cs) |
| HU (1) | HU179734B (cs) |
| IE (1) | IE48623B1 (cs) |
| NO (1) | NO151588C (cs) |
| NZ (1) | NZ191434A (cs) |
| PH (1) | PH15662A (cs) |
| PL (1) | PL121663B1 (cs) |
| PT (1) | PT70130A (cs) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5993054A (ja) * | 1982-11-18 | 1984-05-29 | Asahi Chem Ind Co Ltd | イソキノリンスルホン酸アミド誘導体 |
| JPS61112018A (ja) * | 1984-11-06 | 1986-05-30 | Mitsubishi Chem Ind Ltd | 線溶増強剤 |
| US5585498A (en) * | 1992-03-30 | 1996-12-17 | Synthelabo | Imidazole derivatives useful as synthetic intermediates |
| FR2689130B1 (fr) | 1992-03-30 | 1994-05-27 | Synthelabo | Derives de 1-[2 (arylsulfonylamino)ethyl-1-oxo] piperidine, leur preparation et leur application en therapeutique. |
| GB9209032D0 (en) * | 1992-04-25 | 1992-06-10 | Ciba Geigy Ag | New peptide derivatives |
| JPH06219949A (ja) * | 1993-01-25 | 1994-08-09 | Mitsubishi Kasei Corp | 抗トロンビン剤及びその製造方法 |
| JPH06219948A (ja) * | 1993-01-25 | 1994-08-09 | Mitsubishi Kasei Corp | 抗トロンビン剤及びその製造方法 |
| FR2702220B1 (fr) * | 1993-03-03 | 1995-05-12 | Synthelabo | Dédoublement enzymatique de dérivés de 4-alkyl-2-pipéridine-carboxylate et utilisation des composés obtenus, comme intermédiaires de synthèse. |
| DE69417087T2 (de) * | 1993-04-22 | 1999-07-15 | Mitsubishi Chemical Corp., Tokio/Tokyo | Wässrige Arzneizubereitungen enthaltend Argatroban und Cyclodextrin oder Coffein |
| FR2710066B1 (fr) * | 1993-09-14 | 1995-10-20 | Synthelabo | Dérivés de 1-[2-amino-5-[1-(triphénylméthyl-1H-imidazol-4-yl]-1-oxopentyl]piperidine, leur préparation et leur utilisation comme intermédiaires de synthèse. |
| FR2710067B1 (fr) * | 1993-09-14 | 1995-10-20 | Synthelabo | Procédé de préparation de 2-amino-5-(1H-imidazol-4-yl)-1-oxopentylpipéridine. |
| FR2710061B1 (fr) * | 1993-09-14 | 1995-12-29 | Synthelabo | Acides et chlorures d'acides 1,2,3, 4-tétrahydroquinoléine-8-sulfoniques, et leur utilisation comme intermédiaires de synthèse. |
| PT656348E (pt) * | 1993-12-03 | 2000-10-31 | Hoffmann La Roche | Derivados do acido acetico como medicamentos |
| FR2715566B1 (fr) * | 1994-02-03 | 1996-03-08 | Synthelabo | Solutions aqueuses concentrées d'argatroban. |
| FR2718439B3 (fr) * | 1994-04-12 | 1996-02-09 | Synthelabo | Dérivés de l'acide pipécolique, leur préparation et leur utilisation comme intermédiaires de synthèse. |
| DE4424828A1 (de) * | 1994-07-14 | 1996-01-18 | Thomae Gmbh Dr K | Neue substituierte Arylsulfonamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| GB9505538D0 (en) * | 1995-03-18 | 1995-05-03 | Ciba Geigy Ag | New compounds |
| GB9508622D0 (en) * | 1995-04-28 | 1995-06-14 | Pfizer Ltd | Therapeutic agants |
| FR2735469B1 (fr) * | 1995-06-13 | 1997-07-11 | Synthelabo | N2-(arylsulfonyl)-l-arginylpiperidin-2-carboxylates, leur preparation et leur application en therapeutique |
| FR2747676B1 (fr) * | 1996-04-22 | 1998-06-05 | Synthelabo | Derives de [1-oxo-2-(sulfonylamino)ethyl] piperidine, leur preparation et leur application en therapeutique |
| US5840733A (en) * | 1996-07-01 | 1998-11-24 | Redcell, Canada, Inc. | Methods and compositions for producing novel conjugates of thrombin inhibitors and endogenous carriers resulting in anti-thrombins with extended lifetimes |
| US5925760A (en) * | 1996-08-07 | 1999-07-20 | Mitsubishi Chemical Corporation | Method for preparing N2 -arylsulfonyl-L-argininamides |
| FR2804682B1 (fr) * | 2000-02-09 | 2002-05-03 | Rhodia Chimie Sa | Procede de preparation diastereoselective de piperidines fonctionnalisees en positions 2 et 4 utilisables comme intermediaires de synthese |
| JP2006096668A (ja) * | 2002-11-08 | 2006-04-13 | Ono Pharmaceut Co Ltd | エラスターゼ阻害剤と血液凝固系および／または線溶系酵素阻害剤との組み合わせからなる医薬 |
| CN100427480C (zh) * | 2006-11-10 | 2008-10-22 | 天津市炜杰科技有限公司 | 阿加曲班水合物的制备方法 |
| US7915290B2 (en) | 2008-02-29 | 2011-03-29 | Baxter International Inc. | Argatroban formulations and methods for making and using same |
| CN101914133B (zh) * | 2008-03-07 | 2013-01-30 | 天津市炜杰科技有限公司 | 一种21(s)阿加曲班的定向合成方法 |
| ITPD20080106A1 (it) | 2008-04-07 | 2009-10-08 | Lundbeck Pharmaceuticals Italy Spa | Metodo di preparazione di argatroban monoidrato |
| EP2305646A1 (en) | 2009-10-02 | 2011-04-06 | Enantia, S.L. | A process for the preparation of trans-(2R)-4-substituted-pipecolic acids and esters thereof, and intermediate compounds used therein |
| ITMI20110545A1 (it) | 2011-04-04 | 2012-10-05 | Lundbeck Pharmaceuticals Italy S P A | Metodo per la preparazione di intermedi di processo per la sintesi di argatroban monoidrato |
| CN103570803B (zh) * | 2012-08-30 | 2015-06-03 | 上海科胜药物研发有限公司 | 一种阿加曲班中间体的制备方法 |
| CN104672132B (zh) * | 2013-11-28 | 2017-06-16 | 四川科瑞德制药股份有限公司 | 阿加曲班中间体的合成方法 |
| CN104098647B (zh) * | 2014-06-24 | 2017-12-08 | 安徽省逸欣铭医药科技有限公司 | 阿加曲班类似物及其制备方法和医药用途 |
| CN106928199B (zh) * | 2017-05-08 | 2020-06-09 | 安徽医学高等专科学校 | 一种嘧啶化合物的晶型c的制备方法和用途 |
| CN109912570A (zh) * | 2019-04-04 | 2019-06-21 | 天津药物研究院药业有限责任公司 | 一种阿加曲班中间体酰胺化物的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1131621A (en) * | 1977-01-19 | 1982-09-14 | Shosuke Okamoto | N.sup.2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
-
1979
- 1979-08-14 IE IE1565/79A patent/IE48623B1/en not_active IP Right Cessation
- 1979-08-16 CA CA000333888A patent/CA1135698A/en not_active Expired
- 1979-08-22 DE DE7979103092T patent/DE2963539D1/de not_active Expired
- 1979-08-22 EP EP79103092A patent/EP0008746B1/en not_active Expired
- 1979-08-23 FI FI792637A patent/FI66183C/fi not_active IP Right Cessation
- 1979-08-24 PH PH22953A patent/PH15662A/en unknown
- 1979-08-27 DD DD79215205A patent/DD146600A5/de not_active IP Right Cessation
- 1979-08-28 GR GR59919A patent/GR64905B/el unknown
- 1979-08-28 HU HU79MI654A patent/HU179734B/hu unknown
- 1979-08-29 PT PT70130A patent/PT70130A/pt unknown
- 1979-08-29 CS CS795887A patent/CS228119B2/cs unknown
- 1979-08-29 PL PL1979218008A patent/PL121663B1/pl unknown
- 1979-08-30 NZ NZ191434A patent/NZ191434A/en unknown
- 1979-08-30 DK DK364579A patent/DK152495C/da not_active IP Right Cessation
- 1979-08-30 NO NO792823A patent/NO151588C/no unknown
- 1979-08-31 ES ES483767A patent/ES483767A1/es not_active Expired
- 1979-08-31 AU AU50486/79A patent/AU520342B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE48623B1 (en) | 1985-03-20 |
| NZ191434A (en) | 1984-07-06 |
| NO151588B (no) | 1985-01-21 |
| PH15662A (en) | 1983-03-11 |
| DK364579A (da) | 1980-03-01 |
| GR64905B (en) | 1980-06-07 |
| EP0008746B1 (en) | 1982-08-11 |
| NO792823L (no) | 1980-03-03 |
| PL121663B1 (en) | 1982-05-31 |
| DE2963539D1 (en) | 1982-10-07 |
| ES483767A1 (es) | 1980-04-16 |
| DK152495C (da) | 1988-07-25 |
| HU179734B (en) | 1982-12-28 |
| IE791565L (en) | 1980-02-29 |
| AU520342B2 (en) | 1982-01-28 |
| CA1135698A (en) | 1982-11-16 |
| PT70130A (en) | 1979-09-01 |
| EP0008746A1 (en) | 1980-03-19 |
| FI66183B (fi) | 1984-05-31 |
| PL218008A1 (cs) | 1980-05-05 |
| NO151588C (no) | 1985-05-08 |
| DK152495B (da) | 1988-03-07 |
| AU5048679A (en) | 1980-03-06 |
| FI66183C (fi) | 1984-09-10 |
| FI792637A7 (fi) | 1980-03-01 |
| CS228119B2 (en) | 1984-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |