CA2100228A1 - Phospholipid derivatives - Google Patents
Phospholipid derivativesInfo
- Publication number
- CA2100228A1 CA2100228A1 CA002100228A CA2100228A CA2100228A1 CA 2100228 A1 CA2100228 A1 CA 2100228A1 CA 002100228 A CA002100228 A CA 002100228A CA 2100228 A CA2100228 A CA 2100228A CA 2100228 A1 CA2100228 A1 CA 2100228A1
- Authority
- CA
- Canada
- Prior art keywords
- straight
- chain
- carbon atoms
- alkyl radical
- groups
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000003904 phospholipids Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 231100001018 bone marrow damage Toxicity 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 231100000052 myelotoxic Toxicity 0.000 abstract 1
- 230000002556 myelotoxic effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 208000017520 skin disease Diseases 0.000 abstract 1
- 230000003612 virological effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/106—Adducts, complexes, salts of phosphatides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5532—Seven-(or more) membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- AIDS & HIV (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Compounds of the general formula I
(see formula I) in which: R is a straight-chain or branched alkyl radical having 10 to 24 carbon atoms, which also can contain one to three double or triple bonds; R1 and R2, independently of one another, are hydrogen, or each is a straight-chain or branched saturated alkyl radical having 1 to 6 carbon atoms, a straight-chain or branched unsaturated alkyl radical having 2 to 6 carbon atoms, or a cyclic saturated or unsaturated alkyl radical having 3 to 6 carbon atoms, which also can contain a Cl, OH or NH2 group; and where straight-chain or branched alkyl radicals R1 and R2 also can be bonded together to form a ring; A is a single bond or one of the groups having the formulae -CH2-CH2-CH2-O- (II) -CH2-CH2-O- (III) (see formula IV) -s-(CH2)8-O- (V) (see formula VI) wherein: the groups (II) to (VI) are arranged such that the oxygen atom is bonded to the phosphorus atom of the compound (I); X is an oxygen or sulphur atom, or NH if A is a single bond, or is an oxygen or sulphur atom if A is one of the groups (II) to (VI); y is 0 or a natural number between 1 and 3; and m + n independently of one another are 0 or natural numbers, with the proviso that m + n = 2 to 8;
and pharmaceutically-acceptable salts thereof. These novel phospholipid derivatives are useful for treating tumours, protozoal and fungal diseases, autoimmune diseases, skin diseases, bone marrow damage due to treatment with cytostatic and other myelotoxic agents, and viral diseases.
Preparation and purification methods for the compound are also disclosed.
(see formula I) in which: R is a straight-chain or branched alkyl radical having 10 to 24 carbon atoms, which also can contain one to three double or triple bonds; R1 and R2, independently of one another, are hydrogen, or each is a straight-chain or branched saturated alkyl radical having 1 to 6 carbon atoms, a straight-chain or branched unsaturated alkyl radical having 2 to 6 carbon atoms, or a cyclic saturated or unsaturated alkyl radical having 3 to 6 carbon atoms, which also can contain a Cl, OH or NH2 group; and where straight-chain or branched alkyl radicals R1 and R2 also can be bonded together to form a ring; A is a single bond or one of the groups having the formulae -CH2-CH2-CH2-O- (II) -CH2-CH2-O- (III) (see formula IV) -s-(CH2)8-O- (V) (see formula VI) wherein: the groups (II) to (VI) are arranged such that the oxygen atom is bonded to the phosphorus atom of the compound (I); X is an oxygen or sulphur atom, or NH if A is a single bond, or is an oxygen or sulphur atom if A is one of the groups (II) to (VI); y is 0 or a natural number between 1 and 3; and m + n independently of one another are 0 or natural numbers, with the proviso that m + n = 2 to 8;
and pharmaceutically-acceptable salts thereof. These novel phospholipid derivatives are useful for treating tumours, protozoal and fungal diseases, autoimmune diseases, skin diseases, bone marrow damage due to treatment with cytostatic and other myelotoxic agents, and viral diseases.
Preparation and purification methods for the compound are also disclosed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002511753A CA2511753C (en) | 1992-07-11 | 1993-07-09 | Phospholipid derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4222910A DE4222910A1 (en) | 1992-07-11 | 1992-07-11 | New phospholipid derivatives |
| DEP4222910.3 | 1992-07-11 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002511753A Division CA2511753C (en) | 1992-07-11 | 1993-07-09 | Phospholipid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2100228A1 true CA2100228A1 (en) | 1994-01-12 |
| CA2100228C CA2100228C (en) | 2006-01-24 |
Family
ID=6463031
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002100228A Expired - Lifetime CA2100228C (en) | 1992-07-11 | 1993-07-09 | Phospholipid derivatives |
| CA002511753A Expired - Lifetime CA2511753C (en) | 1992-07-11 | 1993-07-09 | Phospholipid derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002511753A Expired - Lifetime CA2511753C (en) | 1992-07-11 | 1993-07-09 | Phospholipid derivatives |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0579939B1 (en) |
| JP (1) | JP3311431B2 (en) |
| KR (1) | KR100297180B1 (en) |
| CN (1) | CN1039012C (en) |
| AT (1) | ATE176477T1 (en) |
| AU (1) | AU664101B2 (en) |
| BR (1) | BR9302809A (en) |
| CA (2) | CA2100228C (en) |
| CZ (1) | CZ290863B6 (en) |
| DE (2) | DE4222910A1 (en) |
| DK (1) | DK0579939T3 (en) |
| EE (1) | EE03140B1 (en) |
| ES (1) | ES2129053T3 (en) |
| FI (1) | FI111262B (en) |
| GR (1) | GR3029602T3 (en) |
| HR (1) | HRP931046B1 (en) |
| HU (1) | HU218783B (en) |
| IL (1) | IL106289A (en) |
| LT (1) | LT3113B (en) |
| LV (1) | LV10870B (en) |
| MX (1) | MX9304133A (en) |
| NO (1) | NO306468B1 (en) |
| PL (3) | PL177811B1 (en) |
| RU (1) | RU2108336C1 (en) |
| SG (1) | SG46249A1 (en) |
| SI (1) | SI9300365B (en) |
| SK (1) | SK283827B6 (en) |
| TW (1) | TW304956B (en) |
| UA (1) | UA40567C2 (en) |
| YU (1) | YU49079B (en) |
| ZA (1) | ZA934971B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5475234B2 (en) | 2005-01-21 | 2014-04-16 | アステックス・セラピューティクス・リミテッド | Pharmaceutical compounds |
| JP5232009B2 (en) * | 2005-12-19 | 2013-07-10 | エテルナ ツェンタリス ゲゼルシャフト ミット ベシュレンクテル ハフツング | Alkyl phospholipid derivatives having reduced cytotoxicity and uses thereof |
| EP1800684A1 (en) * | 2005-12-20 | 2007-06-27 | Zentaris GmbH | Novel alkyl phospholipid derivatives and uses thereof |
| EP1869981A1 (en) * | 2006-06-21 | 2007-12-26 | Staatliches Weinbauinstitut Freiburg | Alkylphospholipids and lysophospholipids for controlling plant pathogens |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444766A (en) * | 1980-10-21 | 1984-04-24 | Boehringer Mannheim Gmbh | Sulfur-containing phospholipid compounds and therapeutic compositions |
| JPS5984824A (en) * | 1982-11-08 | 1984-05-16 | Takeda Chem Ind Ltd | Antitumor agent |
| DE3530767A1 (en) * | 1985-08-28 | 1987-03-12 | Max Planck Gesellschaft | AGENT AGAINST MULTIPLE Sclerosis |
| CA1280369C (en) * | 1985-12-04 | 1991-02-19 | Hansjorg Eibl | Pharmaceutical with anti-tumor effect |
| JP2512311B2 (en) * | 1986-07-14 | 1996-07-03 | 日本ケミファ株式会社 | Novel glycerin derivative and antihypertensive agent |
| US4962096A (en) * | 1987-03-24 | 1990-10-09 | Nippon Chemiphar Co., Ltd. | Heterocyclic glycerol derivatives and their use as anti-hypertensive agents |
| DE3906952A1 (en) * | 1989-03-04 | 1990-09-06 | Boehringer Mannheim Gmbh | (3- (C (DOWN ARROW)) (DOWN ARROW) (DOWN ARROW) 6 (DOWN ARROW) -C (DOWN ARROW) 1 (DOWN ARROW) (DOWN ARROW) 8 (DOWN ARROW)) ALKANSULFINYL AND 2 SULPHONE -METHOXYMETHYL-PROPYL) - (2-TRIMETHYLAMMONIO-ETHYL) PHOSPHATES, METHOD FOR PRODUCING THE MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE3942933A1 (en) * | 1989-12-23 | 1991-06-27 | Boehringer Mannheim Gmbh | USE OF ALKYLPHOSPHOLIPIDES AS ANTIVIRAL MEDICINAL PRODUCTS AND NEW PHOSPHOLIPID DERIVATIVES |
| DE4114586A1 (en) * | 1991-05-04 | 1992-11-05 | Boehringer Mannheim Gmbh | MEDICINAL PRODUCTS CONTAINING AZACYCLODIPHOSPHONIC ACID DERIVATIVES, NEW AZACYCLODIPHOSPHONIC ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
-
1992
- 1992-07-11 DE DE4222910A patent/DE4222910A1/en not_active Ceased
-
1993
- 1993-06-01 TW TW082104345A patent/TW304956B/zh not_active IP Right Cessation
- 1993-06-03 AT AT93108904T patent/ATE176477T1/en active
- 1993-06-03 DK DK93108904T patent/DK0579939T3/en active
- 1993-06-03 SG SG1996001626A patent/SG46249A1/en unknown
- 1993-06-03 DE DE59309355T patent/DE59309355D1/en not_active Expired - Lifetime
- 1993-06-03 ES ES93108904T patent/ES2129053T3/en not_active Expired - Lifetime
- 1993-06-03 EP EP93108904A patent/EP0579939B1/en not_active Expired - Lifetime
- 1993-06-04 LT LTIP620A patent/LT3113B/en not_active IP Right Cessation
- 1993-06-23 CZ CZ19931249A patent/CZ290863B6/en not_active IP Right Cessation
- 1993-06-28 SK SK670-93A patent/SK283827B6/en not_active IP Right Cessation
- 1993-07-06 YU YU47393A patent/YU49079B/en unknown
- 1993-07-08 PL PL93318679A patent/PL177811B1/en unknown
- 1993-07-08 PL PL93299624A patent/PL173388B1/en unknown
- 1993-07-08 JP JP16911493A patent/JP3311431B2/en not_active Expired - Lifetime
- 1993-07-08 PL PL93318680A patent/PL175607B1/en unknown
- 1993-07-08 NO NO932502A patent/NO306468B1/en not_active IP Right Cessation
- 1993-07-09 ZA ZA934971A patent/ZA934971B/en unknown
- 1993-07-09 HR HR931046A patent/HRP931046B1/en not_active IP Right Cessation
- 1993-07-09 BR BR9302809A patent/BR9302809A/en not_active Application Discontinuation
- 1993-07-09 IL IL10628993A patent/IL106289A/en not_active IP Right Cessation
- 1993-07-09 FI FI933165A patent/FI111262B/en not_active IP Right Cessation
- 1993-07-09 AU AU41864/93A patent/AU664101B2/en not_active Expired
- 1993-07-09 CA CA002100228A patent/CA2100228C/en not_active Expired - Lifetime
- 1993-07-09 SI SI9300365A patent/SI9300365B/en unknown
- 1993-07-09 CA CA002511753A patent/CA2511753C/en not_active Expired - Lifetime
- 1993-07-09 MX MX9304133A patent/MX9304133A/en active IP Right Grant
- 1993-07-09 RU RU93047049A patent/RU2108336C1/en active
- 1993-07-09 HU HU9301992A patent/HU218783B/en unknown
- 1993-07-09 UA UA93002052A patent/UA40567C2/en unknown
- 1993-07-10 KR KR1019930012980A patent/KR100297180B1/en not_active IP Right Cessation
- 1993-07-10 CN CN93108564A patent/CN1039012C/en not_active Expired - Lifetime
- 1993-07-12 LV LVP-93-988A patent/LV10870B/en unknown
-
1994
- 1994-10-25 EE EE9400199A patent/EE03140B1/en unknown
-
1999
- 1999-03-08 GR GR990400689T patent/GR3029602T3/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
