AU640723B2 - 2-formylbenzylphosphonic acid derivatives, their preparation and their use for the treatment of diseases caused by viruses - Google Patents
2-formylbenzylphosphonic acid derivatives, their preparation and their use for the treatment of diseases caused by virusesInfo
- Publication number
- AU640723B2 AU640723B2 AU68304/90A AU6830490A AU640723B2 AU 640723 B2 AU640723 B2 AU 640723B2 AU 68304/90 A AU68304/90 A AU 68304/90A AU 6830490 A AU6830490 A AU 6830490A AU 640723 B2 AU640723 B2 AU 640723B2
- Authority
- AU
- Australia
- Prior art keywords
- viruses
- preparation
- treatment
- diseases caused
- alkynyl
- 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.)
- Ceased
Links
- 241000700605 Viruses Species 0.000 title abstract 2
- 201000010099 disease Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- URYYOODIPZFJIN-UHFFFAOYSA-N (2-formylphenyl)methylphosphonic acid Chemical class OP(O)(=O)CC1=CC=CC=C1C=O URYYOODIPZFJIN-UHFFFAOYSA-N 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- -1 cyclic diester Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000000651 prodrug Chemical group 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The compound of the formula I <IMAGE> in which R represents an aldehyde group or a group which can be converted into an aldehyde, R<1> and R<2> represent alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, hydrogen, sodium, potassium, calcium, magnesium, aluminium, lithium, ammonium or triethylammonium or R<1> and R<2> together form a cyclic diester, R<3> and R<4> represent alkyl, alkenyl, alkynyl, cycloalkyl, hydrogen, alkoxy or halogen, R<5> and R<8> represent alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, alkoxy, phenyl, cyanide, hydroxyl or hydrogen, X, Y or Z represent oxygen or sulphur, or prodrug forms of the compound of the formula I can be used for treatment of diseases caused by viruses. The preparation of these compounds and pharmaceutical preparations which contain them and also their use are described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3942318A DE3942318A1 (en) | 1989-12-21 | 1989-12-21 | 2-FORMYLBENZYLPHOSPHONIC ACID DERIVATIVES, THEIR PRODUCTION AND THE USE THEREOF FOR THE TREATMENT OF DISEASES CAUSED BY VIRUSES |
| DE3942318 | 1989-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6830490A AU6830490A (en) | 1991-06-27 |
| AU640723B2 true AU640723B2 (en) | 1993-09-02 |
Family
ID=6396038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU68304/90A Ceased AU640723B2 (en) | 1989-12-21 | 1990-12-20 | 2-formylbenzylphosphonic acid derivatives, their preparation and their use for the treatment of diseases caused by viruses |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0433928B1 (en) |
| JP (1) | JP2997552B2 (en) |
| KR (1) | KR100191087B1 (en) |
| AT (1) | ATE119908T1 (en) |
| AU (1) | AU640723B2 (en) |
| CA (1) | CA2032772C (en) |
| DE (2) | DE3942318A1 (en) |
| FI (1) | FI102280B1 (en) |
| HU (1) | HU208144B (en) |
| IE (1) | IE67439B1 (en) |
| IL (1) | IL96730A (en) |
| NO (1) | NO179614C (en) |
| NZ (1) | NZ236554A (en) |
| PL (1) | PL288361A1 (en) |
| PT (1) | PT96287B (en) |
| RU (1) | RU2039063C1 (en) |
| ZA (1) | ZA9010269B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006335737A (en) * | 2005-06-03 | 2006-12-14 | Ihara Nikkei Kagaku Kogyo Kk | METHOD FOR PRODUCING BENZO[c]HETEROCYCLIC 5-MEMBERED RING COMPOUND |
| JP2009502964A (en) * | 2005-07-27 | 2009-01-29 | ギリアード サイエンシーズ， インコーポレイテッド | Antiviral phosphonate conjugates for inhibiting HIV |
| JP5789430B2 (en) | 2011-06-27 | 2015-10-07 | イハラニッケイ化学工業株式会社 | Method for producing 2-chloromethylbenzaldehyde, 2-chloromethylbenzaldehyde-containing composition and storage method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918064A (en) * | 1987-10-21 | 1990-04-17 | G. D. Searle & Co. | Phenyl glycines for use in reducing neurotoxic injury |
-
1989
- 1989-12-21 DE DE3942318A patent/DE3942318A1/en not_active Withdrawn
-
1990
- 1990-12-15 AT AT90124305T patent/ATE119908T1/en not_active IP Right Cessation
- 1990-12-15 EP EP90124305A patent/EP0433928B1/en not_active Expired - Lifetime
- 1990-12-15 DE DE59008715T patent/DE59008715D1/en not_active Expired - Fee Related
- 1990-12-19 FI FI906268A patent/FI102280B1/en not_active IP Right Cessation
- 1990-12-19 NZ NZ236554A patent/NZ236554A/en unknown
- 1990-12-19 IL IL9673090A patent/IL96730A/en not_active IP Right Cessation
- 1990-12-20 RU SU4894049/04A patent/RU2039063C1/en not_active IP Right Cessation
- 1990-12-20 CA CA002032772A patent/CA2032772C/en not_active Expired - Fee Related
- 1990-12-20 IE IE462590A patent/IE67439B1/en not_active IP Right Cessation
- 1990-12-20 NO NO905521A patent/NO179614C/en unknown
- 1990-12-20 PL PL28836190A patent/PL288361A1/en unknown
- 1990-12-20 AU AU68304/90A patent/AU640723B2/en not_active Ceased
- 1990-12-20 PT PT96287A patent/PT96287B/en not_active IP Right Cessation
- 1990-12-20 JP JP2417963A patent/JP2997552B2/en not_active Expired - Fee Related
- 1990-12-20 ZA ZA9010269A patent/ZA9010269B/en unknown
- 1990-12-21 KR KR1019900021297A patent/KR100191087B1/en not_active IP Right Cessation
- 1990-12-21 HU HU908412A patent/HU208144B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3942318A1 (en) | 1991-06-27 |
| PT96287A (en) | 1991-09-30 |
| IE904625A1 (en) | 1991-07-17 |
| NO179614B (en) | 1996-08-05 |
| CA2032772C (en) | 2001-10-23 |
| NO905521D0 (en) | 1990-12-20 |
| ATE119908T1 (en) | 1995-04-15 |
| CA2032772A1 (en) | 1991-06-22 |
| IL96730A0 (en) | 1991-09-16 |
| DE59008715D1 (en) | 1995-04-20 |
| AU6830490A (en) | 1991-06-27 |
| PL288361A1 (en) | 1992-07-13 |
| IL96730A (en) | 1996-10-31 |
| NO905521L (en) | 1991-06-24 |
| NZ236554A (en) | 1992-12-23 |
| JPH0616685A (en) | 1994-01-25 |
| FI906268A (en) | 1991-06-22 |
| KR910011874A (en) | 1991-08-07 |
| JP2997552B2 (en) | 2000-01-11 |
| FI102280B (en) | 1998-11-13 |
| RU2039063C1 (en) | 1995-07-09 |
| EP0433928A1 (en) | 1991-06-26 |
| PT96287B (en) | 1998-06-30 |
| ZA9010269B (en) | 1991-09-25 |
| IE67439B1 (en) | 1996-04-03 |
| EP0433928B1 (en) | 1995-03-15 |
| KR100191087B1 (en) | 1999-06-15 |
| HUT56111A (en) | 1991-07-29 |
| FI906268A0 (en) | 1990-12-19 |
| NO179614C (en) | 1996-11-13 |
| HU208144B (en) | 1993-08-30 |
| FI102280B1 (en) | 1998-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH Free format text: FORMER OWNER WAS: HOECHST AKTIENGESELLSCHAFT |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |