ZA200207851B - Dual molecules containing a peroxide derivative, synthesis and therapeutic applications thereof. - Google Patents
Dual molecules containing a peroxide derivative, synthesis and therapeutic applications thereof. Download PDFInfo
- Publication number
- ZA200207851B ZA200207851B ZA200207851A ZA200207851A ZA200207851B ZA 200207851 B ZA200207851 B ZA 200207851B ZA 200207851 A ZA200207851 A ZA 200207851A ZA 200207851 A ZA200207851 A ZA 200207851A ZA 200207851 B ZA200207851 B ZA 200207851B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- radical
- molecules
- group
- molecules according
- Prior art date
Links
- 230000009977 dual effect Effects 0.000 title claims description 12
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 150000002978 peroxides Chemical class 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 thioether radicals Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 230000000078 anti-malarial effect Effects 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- QMNFFXRFOJIOKZ-UHFFFAOYSA-N cycloguanil Chemical compound CC1(C)N=C(N)N=C(N)N1C1=CC=C(Cl)C=C1 QMNFFXRFOJIOKZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 201000004792 malaria Diseases 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical group NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 150000005010 aminoquinolines Chemical class 0.000 claims description 2
- 229950004734 cycloguanil Drugs 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical class CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 2
- 150000003568 thioethers Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 11
- 238000000034 method Methods 0.000 claims 7
- 238000009472 formulation Methods 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 5
- 239000007924 injection Substances 0.000 claims 3
- 238000002347 injection Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical group C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 235000002779 Morchella esculenta Nutrition 0.000 claims 1
- 240000002769 Morchella esculenta Species 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 125000005594 diketone group Chemical group 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 239000006196 drop Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 230000002165 photosensitisation Effects 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 claims 1
- 229960000611 pyrimethamine Drugs 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 150000004901 trioxanes Chemical class 0.000 claims 1
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 5
- 229960004191 artemisinin Drugs 0.000 description 5
- 244000045947 parasite Species 0.000 description 4
- 241000223960 Plasmodium falciparum Species 0.000 description 3
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 239000003430 antimalarial agent Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 2
- 229960003677 chloroquine Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 235000001405 Artemisia annua Nutrition 0.000 description 1
- 240000000011 Artemisia annua Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229960000981 artemether Drugs 0.000 description 1
- FIHJKUPKCHIPAT-AHIGJZGOSA-N artesunate Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@@H](OC(=O)CCC(O)=O)[C@@H]4C FIHJKUPKCHIPAT-AHIGJZGOSA-N 0.000 description 1
- 229960004991 artesunate Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229960001962 mefloquine Drugs 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D323/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0004422A FR2807433B1 (fr) | 2000-04-06 | 2000-04-06 | Molecules duales contenant un derives peroxydique, leur synthese et leurs applications therapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207851B true ZA200207851B (en) | 2004-01-26 |
Family
ID=8848956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207851A ZA200207851B (en) | 2000-04-06 | 2002-09-30 | Dual molecules containing a peroxide derivative, synthesis and therapeutic applications thereof. |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6949569B2 (xx) |
| EP (1) | EP1268470B1 (xx) |
| JP (1) | JP2004521855A (xx) |
| KR (1) | KR100832047B1 (xx) |
| CN (1) | CN1193028C (xx) |
| AP (1) | AP1399A (xx) |
| AR (1) | AR041773A1 (xx) |
| AT (1) | ATE387441T1 (xx) |
| AU (2) | AU4846301A (xx) |
| BR (1) | BR0109885A (xx) |
| CA (1) | CA2405076C (xx) |
| CY (1) | CY1108071T1 (xx) |
| DE (1) | DE60132981T2 (xx) |
| DK (1) | DK1268470T3 (xx) |
| ES (1) | ES2302727T3 (xx) |
| FR (1) | FR2807433B1 (xx) |
| HK (1) | HK1056882A1 (xx) |
| HU (1) | HUP0300428A2 (xx) |
| IL (2) | IL151918A0 (xx) |
| IS (1) | IS6579A (xx) |
| MX (1) | MXPA02009856A (xx) |
| MY (1) | MY128443A (xx) |
| NO (1) | NO329526B1 (xx) |
| NZ (1) | NZ521774A (xx) |
| OA (1) | OA13294A (xx) |
| PT (1) | PT1268470E (xx) |
| WO (1) | WO2001077105A1 (xx) |
| ZA (1) | ZA200207851B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2862304A1 (fr) * | 2003-11-14 | 2005-05-20 | Centre Nat Rech Scient | Molecules duales racemiques ou achirales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques |
| TW200728315A (en) * | 2005-12-06 | 2007-08-01 | Nippon Chemical Ind | Phosphorus transition-metal complex, method of producing the same, and anticancer agent forming the same |
| FR2902100A1 (fr) * | 2006-06-13 | 2007-12-14 | Sanofi Aventis Sa | Molecules duales contenant un derive peroxydique, leur synthese et leurs applications en therapeutique |
| FR2924343A1 (fr) * | 2007-12-04 | 2009-06-05 | Palumed Sa | Nouvelles utilisations therapeutiques de molecules duales contenant un derive peroxydique. |
| WO2012055946A1 (fr) * | 2010-10-27 | 2012-05-03 | Meurice R&D Asbl | Procede de fonctionnalisation de composes insatures |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69614149T2 (de) * | 1995-11-16 | 2002-03-14 | Hoffmann La Roche | Chinolinderivate als antimalariamittel |
-
2000
- 2000-04-06 FR FR0004422A patent/FR2807433B1/fr not_active Expired - Fee Related
-
2001
- 2001-04-04 DE DE60132981T patent/DE60132981T2/de not_active Expired - Lifetime
- 2001-04-04 MX MXPA02009856A patent/MXPA02009856A/es active IP Right Grant
- 2001-04-04 IL IL15191801A patent/IL151918A0/xx unknown
- 2001-04-04 AU AU4846301A patent/AU4846301A/xx active Pending
- 2001-04-04 OA OA1200200308A patent/OA13294A/fr unknown
- 2001-04-04 WO PCT/FR2001/001013 patent/WO2001077105A1/fr active IP Right Grant
- 2001-04-04 KR KR1020027013363A patent/KR100832047B1/ko not_active IP Right Cessation
- 2001-04-04 JP JP2001575578A patent/JP2004521855A/ja active Pending
- 2001-04-04 DK DK01921476T patent/DK1268470T3/da active
- 2001-04-04 AU AU2001248463A patent/AU2001248463B2/en not_active Ceased
- 2001-04-04 NZ NZ521774A patent/NZ521774A/en not_active IP Right Cessation
- 2001-04-04 HU HU0300428A patent/HUP0300428A2/hu unknown
- 2001-04-04 CA CA2405076A patent/CA2405076C/fr not_active Expired - Fee Related
- 2001-04-04 AP APAP/P/2002/002646A patent/AP1399A/en active
- 2001-04-04 US US10/240,929 patent/US6949569B2/en not_active Expired - Fee Related
- 2001-04-04 ES ES01921476T patent/ES2302727T3/es not_active Expired - Lifetime
- 2001-04-04 CN CNB018088066A patent/CN1193028C/zh not_active Expired - Fee Related
- 2001-04-04 EP EP01921476A patent/EP1268470B1/fr not_active Expired - Lifetime
- 2001-04-04 AT AT01921476T patent/ATE387441T1/de active
- 2001-04-04 PT PT01921476T patent/PT1268470E/pt unknown
- 2001-04-04 BR BR0109885-3A patent/BR0109885A/pt not_active IP Right Cessation
- 2001-04-06 AR ARP010101655A patent/AR041773A1/es not_active Application Discontinuation
- 2001-04-06 MY MYPI20011659A patent/MY128443A/en unknown
-
2002
- 2002-09-25 IL IL151918A patent/IL151918A/en not_active IP Right Cessation
- 2002-09-30 ZA ZA200207851A patent/ZA200207851B/en unknown
- 2002-10-03 IS IS6579A patent/IS6579A/is unknown
- 2002-10-04 NO NO20024795A patent/NO329526B1/no not_active IP Right Cessation
-
2004
- 2004-01-06 HK HK03109287A patent/HK1056882A1/xx not_active IP Right Cessation
-
2005
- 2005-08-04 US US11/196,979 patent/US7566710B2/en not_active Expired - Fee Related
-
2008
- 2008-05-26 CY CY20081100544T patent/CY1108071T1/el unknown
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