DE10060145C1 - Chinolin-Derivate, ihre Verwendung und diese enthaltende pharmazeutische Zusammensetzung - Google Patents
Chinolin-Derivate, ihre Verwendung und diese enthaltende pharmazeutische ZusammensetzungInfo
- Publication number
- DE10060145C1 DE10060145C1 DE10060145A DE10060145A DE10060145C1 DE 10060145 C1 DE10060145 C1 DE 10060145C1 DE 10060145 A DE10060145 A DE 10060145A DE 10060145 A DE10060145 A DE 10060145A DE 10060145 C1 DE10060145 C1 DE 10060145C1
- Authority
- DE
- Germany
- Prior art keywords
- quinoline
- hydroxy
- methylquinoline
- radical
- pentynyl
- 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 - Fee Related
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 4
- 206010015037 epilepsy Diseases 0.000 claims abstract description 31
- 108010052164 Sodium Channels Proteins 0.000 claims abstract description 28
- 102000018674 Sodium Channels Human genes 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 230000001419 dependent effect Effects 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000011321 prophylaxis Methods 0.000 claims abstract description 15
- -1 cyclic alkyl radical Chemical class 0.000 claims description 106
- 150000003248 quinolines Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 206010010904 Convulsion Diseases 0.000 claims description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000005840 aryl radicals Chemical class 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 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 description 9
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 208000034308 Grand mal convulsion Diseases 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 208000033001 Complex partial seizures Diseases 0.000 claims description 4
- 206010034010 Parkinsonism Diseases 0.000 claims description 4
- 208000037158 Partial Epilepsies Diseases 0.000 claims description 4
- 206010040703 Simple partial seizures Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 208000003251 Pruritus Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 230000007803 itching Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000000926 neurological effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000036407 pain Effects 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 230000000472 traumatic effect Effects 0.000 claims description 3
- NERSLWZHLIUIBB-UHFFFAOYSA-N 3-[2-(3-hydroxyprop-1-ynoxy)-4-methylquinolin-3-yl]prop-2-yn-1-ol Chemical compound OCC#CC=1C(=NC2=CC=CC=C2C=1C)OC#CCO NERSLWZHLIUIBB-UHFFFAOYSA-N 0.000 claims description 2
- GOBJQRITYJSBPO-UHFFFAOYSA-N 4-methyl-3-oct-1-ynyl-1H-quinolin-2-one Chemical compound OC1=NC2=CC=CC=C2C(=C1C#CCCCCCC)C GOBJQRITYJSBPO-UHFFFAOYSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- SEXLQQVOOOGCND-UHFFFAOYSA-N 1-quinolin-3-yloct-1-yn-3-ol Chemical compound C1=CC=CC2=CC(C#CC(O)CCCCC)=CN=C21 SEXLQQVOOOGCND-UHFFFAOYSA-N 0.000 claims 1
- SMQYITQAYZVWTM-UHFFFAOYSA-N 2,4,6,8-tetramethoxy-3-pent-1-ynylquinoline Chemical compound C(#CCCC)C=1C(=NC2=C(C=C(C=C2C=1OC)OC)OC)OC SMQYITQAYZVWTM-UHFFFAOYSA-N 0.000 claims 1
- GOFDKVYBBUJKNS-UHFFFAOYSA-N 2-(5-ethoxypent-1-ynoxy)-3-(5-ethoxypent-1-ynyl)-4-methylquinoline Chemical compound C1=CC=C2C(C)=C(C#CCCCOCC)C(OC#CCCCOCC)=NC2=C1 GOFDKVYBBUJKNS-UHFFFAOYSA-N 0.000 claims 1
- PFFPIVTXMVQXGT-UHFFFAOYSA-N 3-(3-butoxyprop-1-ynyl)-2,4-dimethoxyquinoline Chemical compound C1=CC=CC2=C(OC)C(C#CCOCCCC)=C(OC)N=C21 PFFPIVTXMVQXGT-UHFFFAOYSA-N 0.000 claims 1
- KEUSKXIWROHZAK-UHFFFAOYSA-N 3-(3-cyclohexyl-3-hydroxyprop-1-ynyl)-4-methyl-1h-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C(C)=C1C#CC(O)C1CCCCC1 KEUSKXIWROHZAK-UHFFFAOYSA-N 0.000 claims 1
- MYPBGCNSFYCIEE-UHFFFAOYSA-N 3-(3-ethoxyprop-1-ynyl)quinoline Chemical compound C1=CC=CC2=CC(C#CCOCC)=CN=C21 MYPBGCNSFYCIEE-UHFFFAOYSA-N 0.000 claims 1
- OKKNGZDIXUYGQA-UHFFFAOYSA-N 3-(3-methoxyoct-1-ynyl)-4-methyl-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(C#CC(OC)CCCCC)=C(C)C2=C1 OKKNGZDIXUYGQA-UHFFFAOYSA-N 0.000 claims 1
- GTJFQARSHZTIBO-UHFFFAOYSA-N 3-(3-methoxyprop-1-ynyl)-4-methyl-1H-quinolin-2-one Chemical compound OC1=NC2=CC=CC=C2C(=C1C#CCOC)C GTJFQARSHZTIBO-UHFFFAOYSA-N 0.000 claims 1
- IYMFWAOINDEKLU-UHFFFAOYSA-N 3-(3-methoxyprop-1-ynyl)quinoline Chemical compound C1=CC=CC2=CC(C#CCOC)=CN=C21 IYMFWAOINDEKLU-UHFFFAOYSA-N 0.000 claims 1
- QXASYWWNRQWPAH-UHFFFAOYSA-N 3-(5-hydroxypent-1-ynyl)-4-methyl-1h-quinolin-2-one Chemical compound C1=CC=C2C(C)=C(C#CCCCO)C(=O)NC2=C1 QXASYWWNRQWPAH-UHFFFAOYSA-N 0.000 claims 1
- BAVNSDFSHSKCFV-UHFFFAOYSA-N 3-but-1-ynylquinoline Chemical compound C1=CC=CC2=CC(C#CCC)=CN=C21 BAVNSDFSHSKCFV-UHFFFAOYSA-N 0.000 claims 1
- NTDGLPUELZKWOF-UHFFFAOYSA-N 3-dec-1-ynylquinoline Chemical compound C1=CC=CC2=CC(C#CCCCCCCCC)=CN=C21 NTDGLPUELZKWOF-UHFFFAOYSA-N 0.000 claims 1
- PQOVDEKMHHZJRY-UHFFFAOYSA-N 3-hex-1-ynyl-2,4,6,8-tetramethoxyquinoline Chemical compound C(#CCCCC)C=1C(=NC2=C(C=C(C=C2C=1OC)OC)OC)OC PQOVDEKMHHZJRY-UHFFFAOYSA-N 0.000 claims 1
- LFZOZQSTHRROEG-UHFFFAOYSA-N 3-hex-1-ynyl-2-methyl-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(C#CCCCC)=C(C)NC2=C1 LFZOZQSTHRROEG-UHFFFAOYSA-N 0.000 claims 1
- LACHGOUWZUDIKR-UHFFFAOYSA-N 3-hex-1-ynyl-4-methyl-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(C#CCCCC)=C(C)C2=C1 LACHGOUWZUDIKR-UHFFFAOYSA-N 0.000 claims 1
- ILTYUQFCUJBWLO-UHFFFAOYSA-N 3-hex-1-ynylquinoline Chemical compound C1=CC=CC2=CC(C#CCCCC)=CN=C21 ILTYUQFCUJBWLO-UHFFFAOYSA-N 0.000 claims 1
- SFQFAGXOXUWPRM-UHFFFAOYSA-N 3-pent-1-ynylquinoline Chemical compound C1=CC=CC2=CC(C#CCCC)=CN=C21 SFQFAGXOXUWPRM-UHFFFAOYSA-N 0.000 claims 1
- BATAIOGYFWEXQV-UHFFFAOYSA-N 3-quinolin-3-ylprop-2-yn-1-ol Chemical compound C1=CC=CC2=CC(C#CCO)=CN=C21 BATAIOGYFWEXQV-UHFFFAOYSA-N 0.000 claims 1
- LEBZLLKCPVTDTG-UHFFFAOYSA-N 4-methyl-3-(2-phenylethynyl)-1h-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C(C)=C1C#CC1=CC=CC=C1 LEBZLLKCPVTDTG-UHFFFAOYSA-N 0.000 claims 1
- PYFJRPMPPNPUQF-UHFFFAOYSA-N 4-methyl-3-(2-trimethylsilylethynyl)-1h-quinolin-2-one Chemical compound C1=CC=C2C(C)=C(C#C[Si](C)(C)C)C(=O)NC2=C1 PYFJRPMPPNPUQF-UHFFFAOYSA-N 0.000 claims 1
- FSEGBIBGOCXVSD-UHFFFAOYSA-N 7-chloro-4-methyl-3-pent-1-ynylquinoline Chemical compound ClC1=CC=C2C(=C(C=NC2=C1)C#CCCC)C FSEGBIBGOCXVSD-UHFFFAOYSA-N 0.000 claims 1
- WENFMPNDAAVKFY-UHFFFAOYSA-N C1=CC=C2C(C)=C(C#CC(=O)OC)C(OC#CC(=O)OC)=NC2=C1 Chemical compound C1=CC=C2C(C)=C(C#CC(=O)OC)C(OC#CC(=O)OC)=NC2=C1 WENFMPNDAAVKFY-UHFFFAOYSA-N 0.000 claims 1
- WKOOFZBWJQCOSV-UHFFFAOYSA-N C1=CC=C2C(C)=C(C#CC(C)(C)O)C(OC#CC(C)(C)O)=NC2=C1 Chemical compound C1=CC=C2C(C)=C(C#CC(C)(C)O)C(OC#CC(C)(C)O)=NC2=C1 WKOOFZBWJQCOSV-UHFFFAOYSA-N 0.000 claims 1
- CLEGMSRPPJJDSF-UHFFFAOYSA-N C1=CC=C2C(C)=C(C#CCCCC)C(OC#CCCCC)=NC2=C1 Chemical compound C1=CC=C2C(C)=C(C#CCCCC)C(OC#CCCCC)=NC2=C1 CLEGMSRPPJJDSF-UHFFFAOYSA-N 0.000 claims 1
- ILNYLJXOLGOADZ-UHFFFAOYSA-N C1=CC=C2C(C)=C(C#CCCCCCC)C(OC#CCCCCCC)=NC2=C1 Chemical compound C1=CC=C2C(C)=C(C#CCCCCCC)C(OC#CCCCCCC)=NC2=C1 ILNYLJXOLGOADZ-UHFFFAOYSA-N 0.000 claims 1
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- NDPDFOZLEMFGTJ-UHFFFAOYSA-N CCCCCC#CC1=CN=C2C=C(C=CC2=C1C)Cl Chemical compound CCCCCC#CC1=CN=C2C=C(C=CC2=C1C)Cl NDPDFOZLEMFGTJ-UHFFFAOYSA-N 0.000 claims 1
- IXUOWKYBDVIQMN-UHFFFAOYSA-N CCOC(=O)C#CC1=C(C2=CC=CC=C2N=C1OC#CC(=O)OC#C)C Chemical compound CCOC(=O)C#CC1=C(C2=CC=CC=C2N=C1OC#CC(=O)OC#C)C IXUOWKYBDVIQMN-UHFFFAOYSA-N 0.000 claims 1
- VXFGITQJHNVYDB-UHFFFAOYSA-N COCCC#CC1=CC2=CC=CC=C2N=C1 Chemical compound COCCC#CC1=CC2=CC=CC=C2N=C1 VXFGITQJHNVYDB-UHFFFAOYSA-N 0.000 claims 1
- VYHRJIAVIYYSEC-UHFFFAOYSA-N COCCCC#CC1=C(C2=CC=CC=C2N=C1OC)OC Chemical compound COCCCC#CC1=C(C2=CC=CC=C2N=C1OC)OC VYHRJIAVIYYSEC-UHFFFAOYSA-N 0.000 claims 1
- NTKLFOJTNGZAEH-UHFFFAOYSA-N ethyl 3-quinolin-3-ylprop-2-ynoate Chemical compound C1=CC=CC2=CC(C#CC(=O)OCC)=CN=C21 NTKLFOJTNGZAEH-UHFFFAOYSA-N 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 230000001788 irregular Effects 0.000 claims 1
- PSBJUJKOOVWPPP-UHFFFAOYSA-N methyl 3-(4-methyl-2-oxo-1h-quinolin-3-yl)prop-2-ynoate Chemical compound C1=CC=C2NC(=O)C(C#CC(=O)OC)=C(C)C2=C1 PSBJUJKOOVWPPP-UHFFFAOYSA-N 0.000 claims 1
- KFEYQXVBDPCLNW-UHFFFAOYSA-N methyl 3-quinolin-3-ylprop-2-ynoate Chemical compound C1=CC=CC2=CC(C#CC(=O)OC)=CN=C21 KFEYQXVBDPCLNW-UHFFFAOYSA-N 0.000 claims 1
- 208000027753 pain disease Diseases 0.000 claims 1
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- 238000011282 treatment Methods 0.000 abstract description 29
- 238000000034 method Methods 0.000 abstract description 25
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 238000012360 testing method Methods 0.000 description 20
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10060145A DE10060145C1 (de) | 2000-12-04 | 2000-12-04 | Chinolin-Derivate, ihre Verwendung und diese enthaltende pharmazeutische Zusammensetzung |
| AU2002216939A AU2002216939A1 (en) | 2000-12-04 | 2001-11-27 | Quinoline derivatives and their use as anti-epileptics |
| PCT/DE2001/004452 WO2002046163A2 (fr) | 2000-12-04 | 2001-11-27 | Derives de quinoleine et leur utilisation |
| DE10195304T DE10195304D2 (de) | 2000-12-04 | 2001-11-27 | Chinolin-Derivative und ihre Verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10060145A DE10060145C1 (de) | 2000-12-04 | 2000-12-04 | Chinolin-Derivate, ihre Verwendung und diese enthaltende pharmazeutische Zusammensetzung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10060145C1 true DE10060145C1 (de) | 2002-06-13 |
Family
ID=7665688
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10060145A Expired - Fee Related DE10060145C1 (de) | 2000-12-04 | 2000-12-04 | Chinolin-Derivate, ihre Verwendung und diese enthaltende pharmazeutische Zusammensetzung |
| DE10195304T Expired - Fee Related DE10195304D2 (de) | 2000-12-04 | 2001-11-27 | Chinolin-Derivative und ihre Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10195304T Expired - Fee Related DE10195304D2 (de) | 2000-12-04 | 2001-11-27 | Chinolin-Derivative und ihre Verwendung |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2002216939A1 (fr) |
| DE (2) | DE10060145C1 (fr) |
| WO (1) | WO2002046163A2 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006132192A1 (fr) * | 2005-06-07 | 2006-12-14 | Dainippon Sumitomo Pharma Co., Ltd. | Nouveau dérivé de 2-quinolone |
| WO2008113006A1 (fr) * | 2007-03-14 | 2008-09-18 | Xenon Pharmaceuticals Inc. | Procédés d'utilisation de composés à base de quinolinone dans le traitement des maladies ou des affections associées aux canaux sodiques |
| WO2023036995A1 (fr) * | 2021-09-13 | 2023-03-16 | Centre National De La Recherche Scientifique | Alcynylcarbinols à cytotoxicité élevée |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL89026A (en) * | 1988-01-29 | 1993-02-21 | Lilly Co Eli | Substituted quinolines and cinnolines, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them |
| US5428037A (en) * | 1993-04-09 | 1995-06-27 | Syntex Pharmaceuticals, Ltd. | Heterocyclic derivatives in the treatment of Ischaemia and related diseases |
| US6008230A (en) * | 1995-10-16 | 1999-12-28 | Fujisawa Pharmaceutical Co., Ltd. | Quinoline compounds as H+ -ATPases |
-
2000
- 2000-12-04 DE DE10060145A patent/DE10060145C1/de not_active Expired - Fee Related
-
2001
- 2001-11-27 DE DE10195304T patent/DE10195304D2/de not_active Expired - Fee Related
- 2001-11-27 WO PCT/DE2001/004452 patent/WO2002046163A2/fr not_active Ceased
- 2001-11-27 AU AU2002216939A patent/AU2002216939A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002046163A2 (fr) | 2002-06-13 |
| DE10195304D2 (de) | 2003-10-23 |
| AU2002216939A1 (en) | 2002-06-18 |
| WO2002046163A3 (fr) | 2003-02-13 |
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| 8100 | Publication of the examined application without publication of unexamined application | ||
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |