NO329162B1 - Fremgangsmate ved fremstilling av quinolin-derivater - Google Patents

Fremgangsmate ved fremstilling av quinolin-derivater Download PDF

Info

Publication number: NO329162B1
Authority: NO; Norway
Prior art keywords: methyl; quinoline; solvent; ethyl; preparation
Prior art date: 2002-06-12

Application number

NO20045703A

Other languages

English (en)

Norwegian (no)

Other versions

NO20045703L (no

Inventor

Karl Jansson

Original Assignee

Active Biotech Ab

Priority date (The priority date 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 date listed.)

2002-06-12

Filing date

2004-12-29

Publication date

2010-08-30

2004-12-29 Application filed by Active Biotech Ab filed Critical Active Biotech Ab

2004-12-29 Publication of NO20045703L publication Critical patent/NO20045703L/no

2010-08-30 Publication of NO329162B1 publication Critical patent/NO329162B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 10
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
239000002904 solvent Substances 0.000 claims abstract description 22
150000001875 compounds Chemical class 0.000 claims abstract description 14
239000000203 mixture Substances 0.000 claims abstract description 13
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims abstract description 9
150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 5
238000009835 boiling Methods 0.000 claims abstract description 4
150000001924 cycloalkanes Chemical class 0.000 claims abstract description 4
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 43
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
-1 methoxy, ethoxy, methylthio, ethylthio, n-propylthio, methylsulfinyl Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
DIKSYHCCYVYKRO-UHFFFAOYSA-N n,5-diethyl-4-hydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound OC=1C2=C(CC)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 DIKSYHCCYVYKRO-UHFFFAOYSA-N 0.000 claims description 3
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
ONDYALNGTUAJDX-UHFFFAOYSA-N tasquinimod Chemical compound OC=1C=2C(OC)=CC=CC=2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(C(F)(F)F)C=C1 ONDYALNGTUAJDX-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
GKWPCEFFIHSJOE-UHFFFAOYSA-N laquinimod Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 GKWPCEFFIHSJOE-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 5
SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
MYQFJMYJVJRSGP-UHFFFAOYSA-N 6-chloro-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC(Cl)=CC=C21 MYQFJMYJVJRSGP-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
230000006181 N-acylation Effects 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229960003522 roquinimex Drugs 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SZCPTRGBOVXVCA-UHFFFAOYSA-N 2-amino-6-chlorobenzoic acid Chemical compound NC1=CC=CC(Cl)=C1C(O)=O SZCPTRGBOVXVCA-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
KJMRWDHBVCNLTQ-UHFFFAOYSA-N N-methylisatoic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)N(C)C2=C1 KJMRWDHBVCNLTQ-UHFFFAOYSA-N 0.000 description 1
230000024932 T cell mediated immunity Effects 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000005784 autoimmunity Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
HFQBTBOMXAXHCA-UHFFFAOYSA-N methyl 3-(n-methylanilino)-3-oxopropanoate Chemical compound COC(=O)CC(=O)N(C)C1=CC=CC=C1 HFQBTBOMXAXHCA-UHFFFAOYSA-N 0.000 description 1
PAIDZDPOJWEZLX-UHFFFAOYSA-N methyl 5-chloro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)OC)=C(O)C2=C1Cl PAIDZDPOJWEZLX-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- 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
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Immunology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO20045703A 2002-06-12 2004-12-29 Fremgangsmate ved fremstilling av quinolin-derivater NO329162B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE0201778A SE0201778D0 (sv)	2002-06-12	2002-06-12	Process for the manufacture of quinoline derivatives
PCT/SE2003/000780 WO2003106424A1 (en)	2002-06-12	2003-05-14	Process for the manufacture of quinoline derivatives

Publications (2)

Publication Number	Publication Date
NO20045703L NO20045703L (no)	2004-12-29
NO329162B1 true NO329162B1 (no)	2010-08-30

Family

ID=20288148

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20045703A NO329162B1 (no)	2002-06-12	2004-12-29	Fremgangsmate ved fremstilling av quinolin-derivater

Country Status (28)

Country	Link
EP (1)	EP1511732B9 (is)
JP (1)	JP4584709B2 (is)
KR (1)	KR100979216B1 (is)
CN (1)	CN100418950C (is)
AT (1)	ATE348814T1 (is)
AU (1)	AU2003228195B2 (is)
BR (1)	BR0311674A (is)
CA (1)	CA2487329C (is)
CY (1)	CY1107555T1 (is)
DE (1)	DE60310554T2 (is)
DK (1)	DK1511732T5 (is)
ES (1)	ES2278160T3 (is)
HR (1)	HRP20050028B1 (is)
IL (1)	IL165155A (is)
IS (1)	IS2975B (is)
ME (1)	ME00435B (is)
MX (1)	MXPA04012276A (is)
NO (1)	NO329162B1 (is)
NZ (1)	NZ536768A (is)
PL (1)	PL210259B1 (is)
PT (1)	PT1511732E (is)
RS (1)	RS51021B (is)
RU (1)	RU2291861C2 (is)
SE (1)	SE0201778D0 (is)
SI (1)	SI1511732T1 (is)
UA (1)	UA78310C2 (is)
WO (1)	WO2003106424A1 (is)
ZA (1)	ZA200409430B (is)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0400235D0 (sv)	2004-02-06	2004-02-06	Active Biotech Ab	New composition containing quinoline compounds
US8314124B2 (en)	2004-02-06	2012-11-20	Active Biotech Ab	Crystalline salts of quinoline compounds and methods for preparing them
PT1937642E (pt)	2005-10-19	2014-11-25	Teva Pharma	Cristais de sódio de laquinimod, e processos para o fabrico dos mesmos
KR20140091778A (ko)	2006-06-12	2014-07-22	테바 파마슈티컬 인더스트리즈 리미티드	안정한 라퀴니모드 제제
ES2375417T3 (es)	2006-11-28	2012-02-29	Valeant Pharmaceuticals International	Análogos 1,4-diamino bicíclicos de retigabina como moduladores de los canales de potasio.
PL2234485T3 (pl)	2007-12-20	2014-06-30	Teva Pharma	Stabilne preparaty lakwinimodu
KR20110048571A (ko)	2008-09-03	2011-05-11	테바 파마슈티컬 인더스트리즈 리미티드	면역 기능을 지닌 ２―옥소―１,２―다이하이드로―퀴놀린 조절제
EP2376456A2 (en) *	2008-12-17	2011-10-19	Actavis Group Ptc Ehf	Highly pure laquinimod or a pharmaceutically acceptable salt thereof
DE102009008851A1 (de)	2009-02-13	2010-08-19	Amw Gmbh	Transdermales System mit Immunmodulator
DE102010048788A1 (de)	2009-02-13	2011-05-19	Amw Gmbh	Transdermales System mit Immunmodulator
KR20160148050A (ko)	2009-07-30	2016-12-23	테바 파마슈티컬 인더스트리즈 리미티드	라퀴니모드를 이용한 크론병의 치료
US9585878B2 (en)	2009-08-10	2017-03-07	Teva Pharmaceutical Industries, Ltd.	Treatment of BDNF-related disorders using laquinimod
DE102010026879A1 (de)	2010-02-11	2011-08-11	AMW GmbH, 83627	Transdermales System mit Immunmodulator
KR20160129093A (ko)	2010-03-03	2016-11-08	테바 파마슈티컬 인더스트리즈 리미티드	라퀴니모드를 이용한 루푸스 신장염의 치료
PH12012501740A1 (en)	2010-03-03	2012-11-12	Teva Pharma	Treatment of rheumatoid arthritis with a combination of laquinimod and methotrexate
EP2590653A4 (en) *	2010-07-09	2014-01-01	Teva Pharma	5-CHLORO-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROCHINOLINE-3-CARBOXAMIDE, SALT THEREOF AND APPLICATIONS THEREOF
DK2590949T5 (en) *	2010-07-09	2016-05-23	Active Biotech Ab	METHOD OF PRODUCING quinoline-3-carboxamides
WO2012006538A1 (en)	2010-07-09	2012-01-12	Teva Pharmaceutical Industries Ltd.	Deuterated n-ethyl-n-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof
EP2537517A1 (en) *	2011-06-22	2012-12-26	Active Biotech AB	Deuterium-enriched 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[(4-trifluoro-methyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
WO2013055907A1 (en)	2011-10-12	2013-04-18	Teva Pharmaceutical Industries Ltd.	Treatment of multiple sclerosis with combination of laquinimod and fingolimod
CN104093310A (zh)	2012-02-03	2014-10-08	泰华制药工业有限公司	拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途
US9284276B2 (en)	2012-02-16	2016-03-15	Teva Pharmaceutical Industries, Ltd.	N-ethyl-N-phenyl-1,2-dihydro-4,5-di-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide, preparation and uses thereof
TW201350467A (zh)	2012-05-08	2013-12-16	Teva Pharma	Ｎ－乙基－４－羥基－１－甲基－５－（甲基（２，３，４，５，６－五羥基己基）胺基）－２－側氧－ｎ－苯基－１，２－二氫喹啉－３－甲醯胺
TW201400117A (zh)	2012-06-05	2014-01-01	Teva Pharma	使用拉喹莫德治療眼發炎疾病
TW201410244A (zh)	2012-08-13	2014-03-16	Teva Pharma	用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ）
CN103626701A (zh) *	2012-08-28	2014-03-12	天津药物研究院	一种制备喹啉衍生物的方法
CN103626702A (zh) *	2012-08-30	2014-03-12	天津药物研究院	一种制备喹啉酮衍生物的方法
US8975279B2 (en)	2012-11-07	2015-03-10	Teva Pharmaceutical Industries, Ltd.	Amine salts of laquinimod
WO2014153145A2 (en) *	2013-03-14	2014-09-25	Teva Pharmaceutical Industries Ltd.	Crystals of laquinimod sodium and improved process for the manufacture thereof
HK1231413A1 (zh)	2014-04-29	2017-12-22	Teva Pharmaceutical Industries Ltd.	用於治疗具有高残疾状况的复发-缓解型多发性硬化症(rrms)的患者的拉喹莫德
ES2631194T3 (es)	2014-09-23	2017-08-29	Active Biotech Ab	Quinolincarboxamidas para usar en el tratamiento del mieloma múltiple
WO2016078921A1 (en)	2014-11-19	2016-05-26	Active Biotech Ab	Quinoline carboxamides for use in the treatment of leukemia
MX2022010327A (es)	2020-03-03	2022-11-09	Active Biotech Ab	Tasquinimod o una sal farmaceuticamente aceptable del mismo para el uso en una terapia combinada.
CN111732540B (zh) *	2020-07-20	2020-11-13	湖南速博生物技术有限公司	一种罗喹美克的制备方法
AU2021313388A1 (en)	2020-07-23	2023-01-19	Erasmus University Medical Center Rotterdam (Erasmus Mc)	S100 proteins as novel therapeutic targets in myeloproliferative neoplasms
JP2024503372A (ja)	2021-01-18	2024-01-25	アクティブバイオテックエイビー	骨髄異形成症候群の処置における使用のためのタスキニモドまたはその薬学的に許容される塩
CA3218977A1 (en)	2021-05-25	2022-12-01	Hans Wannman	A plurality of tasquinimod particles and use thereof
WO2023275248A1 (en)	2021-07-02	2023-01-05	Active Biotech Ab	A pharmaceutical product containing tasquinimod and a method for assessing the purity of said product

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE52670B1 (en) *	1981-03-03	1988-01-20	Leo Ab	Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation
US6077851A (en) *	1998-04-27	2000-06-20	Active Biotech Ab	Quinoline derivatives
SE9801474D0 (sv) *	1998-04-27	1998-04-27	Active Biotech Ab	Quinoline Derivatives
SE9802550D0 (sv) *	1998-07-15	1998-07-15	Active Biotech Ab	Quinoline derivatives
US6121287A (en) *	1998-07-15	2000-09-19	Active Biotech Ab	Quinoline derivatives

2002
- 2002-06-12 SE SE0201778A patent/SE0201778D0/xx unknown
2003
- 2003-05-14 CA CA2487329A patent/CA2487329C/en not_active Expired - Lifetime
- 2003-05-14 AT AT03725956T patent/ATE348814T1/de active
- 2003-05-14 EP EP03725956A patent/EP1511732B9/en not_active Expired - Lifetime
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- 2003-05-14 KR KR1020047020088A patent/KR100979216B1/ko not_active Expired - Lifetime
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- 2003-05-14 WO PCT/SE2003/000780 patent/WO2003106424A1/en not_active Ceased
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Also Published As

Publication number	Publication date
CA2487329C (en)	2010-11-16
AU2003228195B2 (en)	2009-05-28
RS107604A (sr)	2007-02-05
EP1511732B9 (en)	2008-11-12
NO20045703L (no)	2004-12-29
IS2975B (is)	2017-07-15
HRP20050028A2 (en)	2006-02-28
ATE348814T1 (de)	2007-01-15
UA78310C2 (en)	2007-03-15
WO2003106424A1 (en)	2003-12-24
MXPA04012276A (es)	2005-04-08
SI1511732T1 (sl)	2007-06-30
RU2005100054A (ru)	2005-07-10
PL373817A1 (en)	2005-09-19
KR20050016537A (ko)	2005-02-21
EP1511732A1 (en)	2005-03-09
BR0311674A (pt)	2008-01-08
PT1511732E (pt)	2007-03-30
RS51021B (sr)	2010-10-31
IS7550A (is)	2004-11-24
IL165155A0 (en)	2005-12-18
DK1511732T3 (da)	2007-04-30
JP2005535612A (ja)	2005-11-24
DE60310554D1 (de)	2007-02-01
DK1511732T5 (da)	2007-10-01
ES2278160T3 (es)	2007-08-01
CA2487329A1 (en)	2003-12-24
IL165155A (en)	2009-11-18
EP1511732B1 (en)	2006-12-20
CY1107555T1 (el)	2013-03-13
AU2003228195A1 (en)	2003-12-31
RU2291861C2 (ru)	2007-01-20
ZA200409430B (en)	2006-02-22
SE0201778D0 (sv)	2002-06-12
HRP20050028B1 (hr)	2013-07-31
JP4584709B2 (ja)	2010-11-24
KR100979216B1 (ko)	2010-08-31
ME00435B (me)	2011-10-10
DE60310554T2 (de)	2007-11-29
CN1659146A (zh)	2005-08-24
PL210259B1 (pl)	2011-12-30
CN100418950C (zh)	2008-09-17
NZ536768A (en)	2006-10-27

Publication	Publication Date	Title
NO329162B1 (no)	2010-08-30	Fremgangsmate ved fremstilling av quinolin-derivater
US6875869B2 (en)	2005-04-05	Process for the manufacture of quinoline derivatives
US7560557B2 (en)	2009-07-14	Process for the manufacture of quinoline derivatives
KR20050028047A (ko)	2005-03-21	1ｈ-이미다조[4,5-ｃ]퀴놀린-4-프탈이미드 중간체를 통한1ｈ-이미다조[4,5-ｃ]퀴놀린-4-아민의 제조
NO179517B (no)	1996-07-15	Fremgangsmåte for fremstilling av 8-klorkinolonderivater
NO871766L (no)	1987-10-30	Fremgangsmaate for fremstilling av terapeutisk aktive benzo(de)isokinolin-1,3-dioner.
FI86420B (fi)	1992-05-15	Foerfarande foer framstaellning av 1-metylaminokinolin-karboxylsyraderivat.
WO2003010144A2 (en)	2003-02-06	A process for synthesis of fluoroquinolonic derivatives
US11332444B2 (en)	2022-05-17	Method for the hydrolysis of quinolonecarboxylic esters
US6933388B2 (en)	2005-08-23	Process for the synthesis of 3-cyano-6-alkoxy-7-nitro-4-quinolones
JP2003096075A (ja)	2003-04-03	キノロンカルボン酸誘導体の製法
JPH0681744B2 (ja)	1994-10-19	２，４−ジオキシキノリン誘導体の製造方法
JPS62132870A (ja)	1987-06-16	Ｎ−（２−ヒドロキシエチル）−２−メチル−３−カルボン酸アミド−キノキサリン−１，４−ジ−ｎ−オキシドの精製法
JP2001278865A (ja)	2001-10-10	４−アミノキノリン類の製造方法

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