NO323320B1 - Medikament egnet til behandling av ondartede tumorer - Google Patents

Medikament egnet til behandling av ondartede tumorer Download PDF

Info

Publication number: NO323320B1
Authority: NO; Norway
Prior art keywords: methyl; quinoline; oxo; carboxamide; dihydro
Prior art date: 1999-10-25

Application number

NO20021932A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021932L (no

NO20021932D0 (no

Inventor

Anders Bjork

Gunnar Hedlund

Stig Jonsson

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.)

1999-10-25

Filing date

2002-04-24

Publication date

2007-03-12

1999-10-25 Priority claimed from SE9903838A external-priority patent/SE9903838D0/xx

2002-04-24 Application filed by Active Biotech Ab filed Critical Active Biotech Ab

2002-04-24 Publication of NO20021932D0 publication Critical patent/NO20021932D0/no

2002-06-21 Publication of NO20021932L publication Critical patent/NO20021932L/no

2007-03-12 Publication of NO323320B1 publication Critical patent/NO323320B1/no

Links

238000011282 treatment Methods 0.000 title claims abstract description 23
239000003814 drug Substances 0.000 title claims abstract description 14
229940079593 drug Drugs 0.000 title claims description 12
201000011510 cancer Diseases 0.000 title abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 76
238000000034 method Methods 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims description 57
229910052739 hydrogen Inorganic materials 0.000 claims description 57
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
150000002431 hydrogen Chemical class 0.000 claims description 29
239000000460 chlorine Chemical group 0.000 claims description 28
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
239000011737 fluorine Chemical group 0.000 claims description 25
229910052731 fluorine Inorganic materials 0.000 claims description 25
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 24
206010060862 Prostate cancer Diseases 0.000 claims description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
-1 n-butyl-iso-butyl Chemical group 0.000 claims description 18
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
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 claims description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([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
229910052708 sodium Inorganic materials 0.000 claims description 6
XWNYCYLXNGLYKJ-UHFFFAOYSA-N 4-amino-n,1,5-trimethyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound NC=1C2=C(C)C=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 XWNYCYLXNGLYKJ-UHFFFAOYSA-N 0.000 claims description 5
230000037396 body weight Effects 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
QJHXVIRCPDYURC-UHFFFAOYSA-N 5-(dimethylamino)-n-ethyl-4-hydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound OC=1C2=C(N(C)C)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 QJHXVIRCPDYURC-UHFFFAOYSA-N 0.000 claims description 4
AUKZBVKADNQWSZ-UHFFFAOYSA-N 5-methoxy-n,1-dimethyl-4-(methylamino)-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC(OC)=C2C(NC)=C1C(=O)N(C)C1=CC=CC=C1 AUKZBVKADNQWSZ-UHFFFAOYSA-N 0.000 claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
206010006187 Breast cancer Diseases 0.000 claims description 4
208000026310 Breast neoplasm Diseases 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
229910052791 calcium Inorganic materials 0.000 claims description 4
150000001767 cationic compounds Chemical class 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
229960002887 deanol Drugs 0.000 claims description 4
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229910001411 inorganic cation Inorganic materials 0.000 claims description 4
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 4
150000002892 organic cations Chemical class 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
OJWYYSVOSNWCCE-UHFFFAOYSA-N 2-methoxyethyl hypofluorite Chemical compound COCCOF OJWYYSVOSNWCCE-UHFFFAOYSA-N 0.000 claims description 3
CFEOYAOYSLOMIN-UHFFFAOYSA-N 4-amino-5-methoxy-n,1-dimethyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound NC=1C=2C(OC)=CC=CC=2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 CFEOYAOYSLOMIN-UHFFFAOYSA-N 0.000 claims description 3
WVMIJXKUTBQGAK-UHFFFAOYSA-N 5-chloro-n-(4-chlorophenyl)-4-hydroxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(Cl)C=C1 WVMIJXKUTBQGAK-UHFFFAOYSA-N 0.000 claims description 3
210000000481 breast Anatomy 0.000 claims description 3
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 description 3
239000000463 material Substances 0.000 claims description 3
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
OJYGICSISOLYTH-UHFFFAOYSA-N n,1,5-trimethyl-4-(methylamino)-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC(C)=C2C(NC)=C1C(=O)N(C)C1=CC=CC=C1 OJYGICSISOLYTH-UHFFFAOYSA-N 0.000 claims description 3
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 3
VFKZOVNOHFQLGN-UHFFFAOYSA-N 4-chloro-2-oxo-1h-quinoline-3-carboxamide Chemical class C1=CC=C2NC(=O)C(C(=O)N)=C(Cl)C2=C1 VFKZOVNOHFQLGN-UHFFFAOYSA-N 0.000 claims description 2
HNVINGXDDMWQLU-UHFFFAOYSA-N 5-(dimethylamino)-4-hydroxy-n-(4-methoxyphenyl)-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC(OC)=CC=C1N(C)C(=O)C1=C(O)C2=C(N(C)C)C=CC=C2N(C)C1=O HNVINGXDDMWQLU-UHFFFAOYSA-N 0.000 claims description 2
NHDURIXSKYSQOE-UHFFFAOYSA-N 5-bromo-n-ethyl-4-hydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound OC=1C2=C(Br)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 NHDURIXSKYSQOE-UHFFFAOYSA-N 0.000 claims description 2
ODHLTMOBLGQWPW-UHFFFAOYSA-N 5-chloro-n-(2,4-difluorophenyl)-4-hydroxy-n,1-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=C(F)C=C1F ODHLTMOBLGQWPW-UHFFFAOYSA-N 0.000 claims description 2
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NBBLDIJJFFEJGC-UHFFFAOYSA-N 5-chloro-n-ethyl-n-(3-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC(F)=C1 NBBLDIJJFFEJGC-UHFFFAOYSA-N 0.000 claims description 2
RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
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239000002552 dosage form Substances 0.000 claims description 2
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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 2
GFRPIRITMNPYQF-UHFFFAOYSA-N n,5-diethyl-4-hydroxy-n-(3-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound OC=1C2=C(CC)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC(OC)=C1 GFRPIRITMNPYQF-UHFFFAOYSA-N 0.000 claims description 2
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208000008494 pericarditis Diseases 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000012071 phase Substances 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000011301 standard therapy Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
235000019786 weight gain Nutrition 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Quinoline Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

NO20021932A 1999-10-25 2002-04-24 Medikament egnet til behandling av ondartede tumorer NO323320B1 (no)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US16140799P	1999-10-25	1999-10-25
SE9903838A SE9903838D0 (sv)	1999-10-25	1999-10-25	Novel compounds
US21281600P	2000-06-21	2000-06-21
SE0002320A SE0002320D0 (sv)	1999-10-25	2000-06-21	Malignant tumors
PCT/SE2000/002055 WO2001030758A1 (en)	1999-10-25	2000-10-24	Drugs for the treatment of malignant tumours

Publications (3)

Publication Number	Publication Date
NO20021932D0 NO20021932D0 (no)	2002-04-24
NO20021932L NO20021932L (no)	2002-06-21
NO323320B1 true NO323320B1 (no)	2007-03-12

Family

ID=27484521

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20021932A NO323320B1 (no)	1999-10-25	2002-04-24	Medikament egnet til behandling av ondartede tumorer

Country Status (21)

Country	Link
EP (1)	EP1224172B1 (de)
JP (1)	JP3950337B2 (de)
KR (2)	KR100674160B1 (de)
AT (1)	ATE358668T1 (de)
AU (1)	AU775057B2 (de)
CA (1)	CA2386775C (de)
CZ (1)	CZ298534B6 (de)
DE (1)	DE60034240T2 (de)
DK (1)	DK1224172T3 (de)
EE (1)	EE200200207A (de)
ES (1)	ES2280258T3 (de)
HK (1)	HK1049830A1 (de)
HR (1)	HRP20020353A2 (de)
HU (1)	HU229072B1 (de)
IL (2)	IL148782A0 (de)
IS (1)	IS2750B (de)
NO (1)	NO323320B1 (de)
NZ (1)	NZ518296A (de)
SE (1)	SE0002320D0 (de)
UA (1)	UA73748C2 (de)
WO (1)	WO2001030758A1 (de)

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KR20150065951A (ko)	2006-06-12	2015-06-15	테바 파마슈티컬 인더스트리즈 리미티드	안정한 라퀴니모드 제제
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US20100074949A1 (en)	2008-08-13	2010-03-25	William Rowe	Pharmaceutical composition and administration thereof
US12458635B2 (en)	2008-08-13	2025-11-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
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KR20130065728A (ko) *	2010-10-14	2013-06-19	임뮤나르 에이비	Ahr 활성화제로서의 1,2-디히드로-4-히드록시-2-옥소-퀴놀린-3-카르복사닐리드
US8802700B2 (en)	2010-12-10	2014-08-12	Vertex Pharmaceuticals Incorporated	Modulators of ATP-Binding Cassette transporters
EP2537517A1 (de)	2011-06-22	2012-12-26	Active Biotech AB	Deuterium-angereichertes 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[(4-trifluor-methyl)phenyl]-1,2-dihydrochinolin-3-carboxamid
JP2015511583A (ja)	2012-02-27	2015-04-20	バーテックスファーマシューティカルズインコーポレイテッドＶｅｒｔｅｘＰｈａｒｍａｃｅｕｔｉｃａｌｓＩｎｃｏｒｐｏｒａｔｅｄ	薬学的組成物およびその投与
MX2015005632A (es) *	2012-11-07	2016-02-05	Teva Pharma	Sales de amina de laquinimod.
EP2970129A2 (de)	2013-03-14	2016-01-20	Teva Pharmaceutical Industries Ltd.	Kristalle aus laquinimodnatrium und verbessertes verfahren zur herstellung davon
WO2016042112A1 (en)	2014-09-23	2016-03-24	Active Biotech Ab	Quinoline carboxamides for use in the treatment of multiple myeloma
CN107250113B (zh)	2014-10-07	2019-03-29	弗特克斯药品有限公司	囊性纤维化跨膜传导调节蛋白的调节剂的共晶
ES2663836T3 (es)	2014-11-19	2018-04-17	Active Biotech Ab	Carboxamidas de quinolina para su uso en el tratamiento de leucemia
US11826363B2 (en)	2017-10-13	2023-11-28	Ono Pharmaceutical Co., Ltd.	Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient
US12478621B2 (en) *	2019-11-28	2025-11-25	Deutsches Krebsforschungszentrum	Substituted aminoquinolones as dgkalpha inhibitors for immune activation
CA3168070A1 (en)	2020-03-03	2021-09-10	Active Biotech Ab	Tasquinimod or a pharmaceutically acceptable salt thereof for use in combination therapy
AU2021275994A1 (en) *	2020-05-21	2022-12-22	Stemsynergy Therapeutics, Inc.	Notch inhibitors and uses thereof
PL4277628T3 (pl)	2021-01-18	2026-02-09	Active Biotech Ab	Taskwinimod lub jego farmaceutycznie dopuszczalna sól do stosowania w leczeniu zespołu mielodysplastycznego
JP2024520307A (ja)	2021-05-25	2024-05-24	アクティブバイオテックエイビー	複数のタスキニモド粒子およびその使用
JP2024524158A (ja)	2021-07-02	2024-07-05	アクティブバイオテックエイビー	タスキニモドを含有する医薬製品および前記製品の純度を評価する方法
AR126963A1 (es)	2021-09-13	2023-12-06	Lilly Co Eli	Agonistas de ahr
TWI838849B (zh)	2021-09-13	2024-04-11	美商美國禮來大藥廠	Ahr促效劑
EP4452946A4 (de) *	2021-12-20	2025-11-26	Univ Johns Hopkins	Verbindungen zur behandlung von krebs

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GB9108547D0 (en) *	1991-04-22	1991-06-05	Fujisawa Pharmaceutical Co	Quinoline derivatives
GB9404378D0 (en) *	1994-03-07	1994-04-20	Fujisawa Pharmaceutical Co	Quinoline derivatives
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US6121287A (en) *	1998-07-15	2000-09-19	Active Biotech Ab	Quinoline derivatives

2000
- 2000-06-21 SE SE0002320A patent/SE0002320D0/xx unknown
- 2000-10-24 UA UA2002032524A patent/UA73748C2/uk unknown
- 2000-10-24 DE DE60034240T patent/DE60034240T2/de not_active Expired - Lifetime
- 2000-10-24 HK HK03100644.7A patent/HK1049830A1/zh unknown
- 2000-10-24 WO PCT/SE2000/002055 patent/WO2001030758A1/en not_active Ceased
- 2000-10-24 ES ES00973329T patent/ES2280258T3/es not_active Expired - Lifetime
- 2000-10-24 CA CA002386775A patent/CA2386775C/en not_active Expired - Fee Related
- 2000-10-24 EE EEP200200207A patent/EE200200207A/xx unknown
- 2000-10-24 AT AT00973329T patent/ATE358668T1/de not_active IP Right Cessation
- 2000-10-24 IL IL14878200A patent/IL148782A0/xx active IP Right Grant
- 2000-10-24 JP JP2001533112A patent/JP3950337B2/ja not_active Expired - Fee Related
- 2000-10-24 AU AU11851/01A patent/AU775057B2/en not_active Ceased
- 2000-10-24 KR KR1020067008739A patent/KR100674160B1/ko not_active Expired - Fee Related
- 2000-10-24 CZ CZ20021293A patent/CZ298534B6/cs not_active IP Right Cessation
- 2000-10-24 NZ NZ518296A patent/NZ518296A/xx not_active IP Right Cessation
- 2000-10-24 DK DK00973329T patent/DK1224172T3/da active
- 2000-10-24 KR KR1020027005077A patent/KR100597938B1/ko not_active Expired - Fee Related
- 2000-10-24 EP EP00973329A patent/EP1224172B1/de not_active Expired - Lifetime
- 2000-10-24 HR HR20020353A patent/HRP20020353A2/hr not_active Application Discontinuation
- 2000-10-24 HU HU0203238A patent/HU229072B1/hu not_active IP Right Cessation
2002
- 2002-03-20 IL IL148782A patent/IL148782A/en not_active IP Right Cessation
- 2002-04-02 IS IS6329A patent/IS2750B/is unknown
- 2002-04-24 NO NO20021932A patent/NO323320B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
UA73748C2 (en)	2005-09-15
IL148782A0 (en)	2002-09-12
IS6329A (is)	2002-04-02
HUP0203238A2 (hu)	2003-01-28
CZ20021293A3 (cs)	2002-07-17
KR20060054496A (ko)	2006-05-22
NO20021932L (no)	2002-06-21
KR100597938B1 (ko)	2006-07-06
JP3950337B2 (ja)	2007-08-01
HUP0203238A3 (en)	2003-05-28
DE60034240T2 (de)	2007-12-20
CA2386775A1 (en)	2001-05-03
KR20020043646A (ko)	2002-06-10
AU775057B2 (en)	2004-07-15
NZ518296A (en)	2003-06-30
SE0002320D0 (sv)	2000-06-21
HRP20020353A2 (en)	2005-10-31
HU229072B1 (en)	2013-07-29
IL148782A (en)	2007-05-15
CZ298534B6 (cs)	2007-10-31
KR100674160B1 (ko)	2007-01-24
JP2003512454A (ja)	2003-04-02
AU1185101A (en)	2001-05-08
NO20021932D0 (no)	2002-04-24
EP1224172A1 (de)	2002-07-24
CA2386775C (en)	2004-07-13
DE60034240D1 (de)	2007-05-16
HK1049830A1 (zh)	2003-05-30
WO2001030758A1 (en)	2001-05-03
EP1224172B1 (de)	2007-04-04
ES2280258T3 (es)	2007-09-16
IS2750B (is)	2011-08-15
EE200200207A (et)	2003-06-16
DK1224172T3 (da)	2007-08-13
ATE358668T1 (de)	2007-04-15

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2019-05-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
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