ES2216528T3 - Derivados de benflumetol y su uso contra protozoos y trematodos parasitarios. - Google Patents
Derivados de benflumetol y su uso contra protozoos y trematodos parasitarios.Info
- Publication number
- ES2216528T3 ES2216528T3 ES99931151T ES99931151T ES2216528T3 ES 2216528 T3 ES2216528 T3 ES 2216528T3 ES 99931151 T ES99931151 T ES 99931151T ES 99931151 T ES99931151 T ES 99931151T ES 2216528 T3 ES2216528 T3 ES 2216528T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- salt
- acid
- compounds
- 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.)
- Expired - Lifetime
Links
- 241000869417 Trematodes Species 0.000 title claims abstract description 8
- DYLGFOYVTXJFJP-MYYYXRDXSA-N lumefantrine Chemical class C12=CC(Cl)=CC=C2C=2C(C(O)CN(CCCC)CCCC)=CC(Cl)=CC=2\C1=C/C1=CC=C(Cl)C=C1 DYLGFOYVTXJFJP-MYYYXRDXSA-N 0.000 title description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 150000003839 salts Chemical group 0.000 claims abstract description 72
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 230000001225 therapeutic effect Effects 0.000 claims description 11
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 230000000069 prophylactic effect Effects 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 239000013066 combination product Substances 0.000 claims 1
- 229940127555 combination product Drugs 0.000 claims 1
- 229960004985 lumefantrine Drugs 0.000 description 42
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- 239000002253 acid Substances 0.000 description 25
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- 241000223960 Plasmodium falciparum Species 0.000 description 16
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- 239000002904 solvent Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- GHZGTMGBTVNGPR-UHFFFAOYSA-N 1-[2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]-2-(pentylamino)ethanol Chemical compound C12=CC(Cl)=CC=C2C=2C(C(O)CNCCCCC)=CC(Cl)=CC=2C1=CC1=CC=C(Cl)C=C1 GHZGTMGBTVNGPR-UHFFFAOYSA-N 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 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 6
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 229960001962 mefloquine Drugs 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- HFMDCMBRQMRRCX-UHFFFAOYSA-N 1-[2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]-2-(methylamino)ethanol Chemical compound C12=CC(Cl)=CC=C2C=2C(C(O)CNC)=CC(Cl)=CC=2C1=CC1=CC=C(Cl)C=C1 HFMDCMBRQMRRCX-UHFFFAOYSA-N 0.000 description 5
- XDCOYBQVEVSNNB-UHFFFAOYSA-N 4-[(7-naphthalen-2-yl-1-benzothiophen-2-yl)methylamino]butanoic acid Chemical compound OC(=O)CCCNCc1cc2cccc(-c3ccc4ccccc4c3)c2s1 XDCOYBQVEVSNNB-UHFFFAOYSA-N 0.000 description 5
- BLUAFEHZUWYNDE-XRNKLDBLSA-N chembl77 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4C31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-XRNKLDBLSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 241000224016 Plasmodium Species 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
- PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- QMNFFXRFOJIOKZ-UHFFFAOYSA-N cycloguanil Chemical group CC1(C)N=C(N)N=C(N)N1C1=CC=C(Cl)C=C1 QMNFFXRFOJIOKZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical class CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/38—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings with rings other than six-membered aromatic rings being part of the carbon skeleton
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1351/98 | 1998-06-25 | ||
| CH135198 | 1998-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2216528T3 true ES2216528T3 (es) | 2004-10-16 |
Family
ID=4208448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99931151T Expired - Lifetime ES2216528T3 (es) | 1998-06-25 | 1999-06-23 | Derivados de benflumetol y su uso contra protozoos y trematodos parasitarios. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6329552B2 (https=) |
| EP (1) | EP1089961B1 (https=) |
| JP (1) | JP4355450B2 (https=) |
| CN (1) | CN1183097C (https=) |
| AT (1) | ATE259346T1 (https=) |
| AU (1) | AU4776399A (https=) |
| BR (1) | BRPI9912208B8 (https=) |
| CA (1) | CA2335685C (https=) |
| CO (1) | CO5040050A1 (https=) |
| ES (1) | ES2216528T3 (https=) |
| ID (1) | ID27500A (https=) |
| MY (1) | MY117662A (https=) |
| PE (1) | PE20000703A1 (https=) |
| PT (1) | PT1089961E (https=) |
| TW (2) | TW200528419A (https=) |
| WO (1) | WO1999067197A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104093689A (zh) * | 2012-01-31 | 2014-10-08 | 剑桥显示技术有限公司 | 聚合物 |
| CN111320547B (zh) * | 2020-04-03 | 2022-05-20 | 南京昊绿生物科技有限公司 | 一种苯芴醇-d9的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1029680C (zh) * | 1988-11-10 | 1995-09-06 | 军事医学科学院微生物流行病研究所 | 抗疟新药苯芴醇的合成新工艺 |
| CN1058717A (zh) * | 1990-08-08 | 1992-02-19 | 中国人民解放军军事医学科学院微生物流行病研究所 | 抗疟新药—复方蒿甲醚及其制备方法 |
-
1999
- 1999-06-11 CO CO99036913A patent/CO5040050A1/es unknown
- 1999-06-23 ES ES99931151T patent/ES2216528T3/es not_active Expired - Lifetime
- 1999-06-23 CA CA002335685A patent/CA2335685C/en not_active Expired - Lifetime
- 1999-06-23 MY MYPI99002590A patent/MY117662A/en unknown
- 1999-06-23 AU AU47763/99A patent/AU4776399A/en not_active Abandoned
- 1999-06-23 PE PE1999000560A patent/PE20000703A1/es not_active IP Right Cessation
- 1999-06-23 PT PT99931151T patent/PT1089961E/pt unknown
- 1999-06-23 EP EP99931151A patent/EP1089961B1/en not_active Expired - Lifetime
- 1999-06-23 BR BRPI9912208A patent/BRPI9912208B8/pt not_active IP Right Cessation
- 1999-06-23 ID IDW20002736A patent/ID27500A/id unknown
- 1999-06-23 AT AT99931151T patent/ATE259346T1/de active
- 1999-06-23 JP JP2000555853A patent/JP4355450B2/ja not_active Expired - Lifetime
- 1999-06-23 CN CNB998096180A patent/CN1183097C/zh not_active Expired - Lifetime
- 1999-06-23 WO PCT/EP1999/004355 patent/WO1999067197A1/en not_active Ceased
- 1999-07-13 TW TW094115936A patent/TW200528419A/zh unknown
- 1999-07-13 TW TW088110752A patent/TWI250141B/zh not_active IP Right Cessation
-
2000
- 2000-12-22 US US09/746,041 patent/US6329552B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1035712A1 (en) | 2001-12-07 |
| ID27500A (id) | 2001-04-12 |
| MY117662A (en) | 2004-07-31 |
| BRPI9912208B8 (pt) | 2021-05-25 |
| EP1089961A1 (en) | 2001-04-11 |
| CN1312794A (zh) | 2001-09-12 |
| PE20000703A1 (es) | 2000-08-23 |
| PT1089961E (pt) | 2004-06-30 |
| EP1089961B1 (en) | 2004-02-11 |
| WO1999067197A1 (en) | 1999-12-29 |
| JP2002518467A (ja) | 2002-06-25 |
| TW200528419A (en) | 2005-09-01 |
| CA2335685A1 (en) | 1999-12-29 |
| AU4776399A (en) | 2000-01-10 |
| CO5040050A1 (es) | 2001-05-29 |
| BR9912208A (pt) | 2001-04-10 |
| CN1183097C (zh) | 2005-01-05 |
| CA2335685C (en) | 2009-08-11 |
| JP4355450B2 (ja) | 2009-11-04 |
| ATE259346T1 (de) | 2004-02-15 |
| TWI250141B (en) | 2006-03-01 |
| US6329552B2 (en) | 2001-12-11 |
| BRPI9912208B1 (pt) | 2016-04-19 |
| US20010014699A1 (en) | 2001-08-16 |
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