SK3632002A3 - Piperidine quinolyl propyl derivatives, preparation method and compositions containing same - Google Patents

Piperidine quinolyl propyl derivatives, preparation method and compositions containing same Download PDF

Info

Publication number: SK3632002A3
Authority: SK; Slovakia
Prior art keywords: propyl; piperidine; methoxyquinolin; acetic acid; group
Prior art date: 1999-09-17

Application number

SK363-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Jean-Luc Malleron

Michel Tabart

Jean-Christophe Carry

Michel Evers

Ahmad Youssef El

Serge Mignani

Fabrice Viviani

Michel Cheve

Original Assignee

Aventis Pharma Sa

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.)

1999-09-17

Filing date

2000-09-14

Publication date

2003-04-01

2000-09-14 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2003-04-01 Publication of SK3632002A3 publication Critical patent/SK3632002A3/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims description 260
-1 4-phenylbuten-3-yl Chemical group 0.000 claims abstract description 2689
125000000217 alkyl group Chemical group 0.000 claims abstract description 53
125000005843 halogen group Chemical group 0.000 claims abstract description 38
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 32
125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 21
229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
125000005842 heteroatom Chemical group 0.000 claims abstract description 19
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
125000005366 cycloalkylthio group Chemical group 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 1954
239000002253 acid Substances 0.000 claims description 761
WKXRHAACRPUBIC-UHFFFAOYSA-N 2-piperidin-1-ium-3-ylacetate Chemical compound OC(=O)CC1CCCNC1 WKXRHAACRPUBIC-UHFFFAOYSA-N 0.000 claims description 254
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 163
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical group 0.000 claims description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
239000001301 oxygen Chemical group 0.000 claims description 19
239000011593 sulfur Chemical group 0.000 claims description 19
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 10
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125000004122 cyclic group Chemical group 0.000 claims description 9
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125000004468 heterocyclylthio group Chemical group 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
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238000006251 dihalogenation reaction Methods 0.000 claims description 2
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239000008194 pharmaceutical composition Substances 0.000 claims description 2
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241000194017 Streptococcus Species 0.000 abstract description 2
238000001727 in vivo Methods 0.000 abstract description 2
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125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract 1
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125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 34
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 34
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 32
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 30
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 28
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125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 21
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 19
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 17
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239000002904 solvent Substances 0.000 description 17
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239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
BNTFCVMJHBNJAR-UHFFFAOYSA-N n,n-diethyl-1,1,2,3,3,3-hexafluoropropan-1-amine Chemical compound CCN(CC)C(F)(F)C(F)C(F)(F)F BNTFCVMJHBNJAR-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
238000000053 physical method Methods 0.000 description 1
BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
USISRUCGEISZIB-UHFFFAOYSA-N piperidin-3-one Chemical compound O=C1CCCNC1 USISRUCGEISZIB-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000004360 trifluorophenyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

SK363-2002A 1999-09-17 2000-09-14 Piperidine quinolyl propyl derivatives, preparation method and compositions containing same SK3632002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9911679A FR2798656B1 (fr)	1999-09-17	1999-09-17	Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent
PCT/FR2000/002541 WO2001025227A2 (fr)	1999-09-17	2000-09-14	Derives de la quinolyl propyl piperidine et leur utilisation en tant que antibacteriens

Publications (1)

Publication Number	Publication Date
SK3632002A3 true SK3632002A3 (en)	2003-04-01

Family

ID=9549990

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK363-2002A SK3632002A3 (en)	1999-09-17	2000-09-14	Piperidine quinolyl propyl derivatives, preparation method and compositions containing same

Country Status (30)

Country	Link
EP (2)	EP1218370B1 (de)
JP (1)	JP2004527448A (de)
KR (1)	KR20020038757A (de)
CN (1)	CN1374959A (de)
AP (1)	AP2002002459A0 (de)
AT (1)	ATE284399T1 (de)
AU (1)	AU7429500A (de)
BG (1)	BG106524A (de)
BR (1)	BR0014060A (de)
CA (1)	CA2383836A1 (de)
CZ (1)	CZ2002940A3 (de)
DE (2)	DE60016611T2 (de)
DZ (1)	DZ3195A1 (de)
EA (1)	EA005183B1 (de)
EE (1)	EE200200138A (de)
FR (1)	FR2798656B1 (de)
GE (1)	GEP20043223B (de)
HR (1)	HRP20020214A2 (de)
HU (1)	HUP0204283A3 (de)
IL (1)	IL148720A0 (de)
MA (1)	MA26820A1 (de)
MX (1)	MXPA02001979A (de)
NO (1)	NO20021253L (de)
OA (1)	OA12022A (de)
PL (1)	PL354809A1 (de)
SK (1)	SK3632002A3 (de)
TN (1)	TNSN00184A1 (de)
WO (1)	WO2001025227A2 (de)
YU (1)	YU19002A (de)
ZA (1)	ZA200202073B (de)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9822440D0 (en)	1998-10-14	1998-12-09	Smithkline Beecham Plc	Medicaments
GB9917408D0 (en)	1999-07-23	1999-09-22	Smithkline Beecham Plc	Compounds
GB9917406D0 (en)	1999-07-23	1999-09-22	Smithkline Beecham Plc	Compounds
IL154107A0 (en)	2000-07-26	2003-07-31	Smithkline Beecham Plc	Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity
GB0031086D0 (en) *	2000-12-20	2001-01-31	Smithkline Beecham Plc	Medicaments
GB0101577D0 (en)	2001-01-22	2001-03-07	Smithkline Beecham Plc	Compounds
GB0112836D0 (en)	2001-05-25	2001-07-18	Smithkline Beecham Plc	Medicaments
GB0112834D0 (en)	2001-05-25	2001-07-18	Smithkline Beecham Plc	Medicaments
AU2003239302A1 (en)	2002-01-29	2003-09-02	Glaxo Group Limited	Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them
WO2003064421A1 (en)	2002-01-29	2003-08-07	Glaxo Group Limited	Aminopiperidine derivatives
TW200409637A (en)	2002-06-26	2004-06-16	Glaxo Group Ltd	Compounds
TW200406413A (en)	2002-06-26	2004-05-01	Glaxo Group Ltd	Compounds
FR2842807A1 (fr) *	2002-07-23	2004-01-30	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, procede et intermediaires de preparation et compositions les renfermant
FR2844268B1 (fr) *	2002-09-11	2004-10-22	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, leurs procedes et intermediaires de preparation et les compositions qui les contiennent
FR2844270B1 (fr) *	2002-09-11	2006-05-19	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, leur procede et intermediaires de preparation et les compositions qui les contiennent
BR0315221A (pt) *	2002-10-10	2005-08-23	Morphochem Ag Komb Chemie	Compostos com atividade antibacteriana
AU2003303956A1 (en)	2002-11-05	2004-11-23	Smithkline Beecham Corporation	Antibacterial agents
AU2003291227A1 (en)	2002-11-05	2004-06-07	Smithkline Beecham Corporation	Antibacterial agents
WO2004050036A2 (en)	2002-12-04	2004-06-17	Glaxo Group Limited	Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents
EP1799674B1 (de) *	2004-10-05	2010-05-05	Actelion Pharmaceuticals Ltd.	Neue piperidin-antibiotika
CA2581057A1 (en) *	2004-10-05	2006-04-13	Actelion Pharmaceuticals Ltd	New piperidine antibiotics
JP2008528586A (ja)	2005-01-25	2008-07-31	グラクソグループリミテッド	抗菌剤
US7709472B2 (en)	2005-01-25	2010-05-04	Glaxo Group Limited	Antibacterial agents
JP2008528588A (ja)	2005-01-25	2008-07-31	グラクソグループリミテッド	抗菌剤
WO2006081264A1 (en)	2005-01-25	2006-08-03	Glaxo Group Limited	Antibacterial agents
WO2007086016A1 (en)	2006-01-26	2007-08-02	Actelion Pharmaceuticals Ltd	Tetrahydropyrane antibiotics
ATE481406T1 (de)	2006-04-06	2010-10-15	Glaxo Group Ltd	Pyrrolochinoxalinonderivate als antibakterielle mittel
GB0613208D0 (en)	2006-07-03	2006-08-09	Glaxo Group Ltd	Compounds
EP1992628A1 (de)	2007-05-18	2008-11-19	Glaxo Group Limited	Derivate und Analoge von N-Ethylquinolonen und N-Ethylazaquinolonen
AU2008249745B2 (en) *	2007-05-09	2012-01-12	Pfizer Inc.	Substituted heterocyclic derivatives and compositions and their pharmaceutical use as antibacterials
EP2080761A1 (de)	2008-01-18	2009-07-22	Glaxo Group Limited	Verbindungen
EP2352734A1 (de)	2008-10-17	2011-08-10	Glaxo Group Limited	Als antibakterielle mittel verwendete tricyclische stickstoffverbindungen
JP5653935B2 (ja)	2009-01-15	2015-01-14	グラクソグループリミテッドＧｌａｘｏＧｒｏｕｐＬｉｍｉｔｅｄ	抗菌薬として有用なナフチリジン―２（１ｈ）−オン化合物
EP3057948B1 (de) *	2013-10-14	2018-03-14	Eisai R&D Management Co., Ltd.	Selektiv substituierte chinolinderivate
EP3639824A1 (de)	2014-08-22	2020-04-22	GlaxoSmithKline Intellectual Property Development Limited	Tricyclische stickstoffhaltige verbindungen zur behandlung einer infektion mit neisseria gonorrhoea
UY36851A (es)	2015-08-16	2017-03-31	Glaxosmithkline Ip Dev Ltd	Compuestos para uso en aplicaciones antibacterianas
SG11201804170RA (en)	2015-12-17	2018-06-28	Merck Patent Gmbh	Polycyclic tlr7/8 antagonists and use thereof in the treatment of immune disorders
EP3497094B1 (de)	2016-08-08	2023-02-15	Merck Patent GmbH	Tlr7/8-antagonisten und verwendungen davon

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1051413B1 (de) *	1998-01-26	2003-06-04	SmithKline Beecham plc	Chinolinderivate als antibakterielles arzneimittel
EP1144404A1 (de) *	1999-01-20	2001-10-17	Smithkline Beecham Plc	Piperidinylchinoline als proteintyrosinkinasehemmer

1999
- 1999-09-17 FR FR9911679A patent/FR2798656B1/fr not_active Expired - Fee Related
2000
- 2000-09-14 EA EA200200374A patent/EA005183B1/ru not_active IP Right Cessation
- 2000-09-14 EE EEP200200138A patent/EE200200138A/xx unknown
- 2000-09-14 HU HU0204283A patent/HUP0204283A3/hu unknown
- 2000-09-14 EP EP00962637A patent/EP1218370B1/de not_active Expired - Lifetime
- 2000-09-14 CZ CZ2002940A patent/CZ2002940A3/cs unknown
- 2000-09-14 MX MXPA02001979A patent/MXPA02001979A/es unknown
- 2000-09-14 PL PL00354809A patent/PL354809A1/xx not_active Application Discontinuation
- 2000-09-14 DE DE60016611T patent/DE60016611T2/de not_active Expired - Fee Related
- 2000-09-14 SK SK363-2002A patent/SK3632002A3/sk unknown
- 2000-09-14 HR HR20020214A patent/HRP20020214A2/hr not_active Application Discontinuation
- 2000-09-14 BR BR0014060-0A patent/BR0014060A/pt not_active IP Right Cessation
- 2000-09-14 KR KR1020027003547A patent/KR20020038757A/ko not_active Ceased
- 2000-09-14 WO PCT/FR2000/002541 patent/WO2001025227A2/fr not_active Ceased
- 2000-09-14 DZ DZ003195A patent/DZ3195A1/xx active
- 2000-09-14 CA CA002383836A patent/CA2383836A1/fr not_active Abandoned
- 2000-09-14 AP APAP/P/2002/002459A patent/AP2002002459A0/en unknown
- 2000-09-14 AU AU74295/00A patent/AU7429500A/en not_active Abandoned
- 2000-09-14 CN CN00813020A patent/CN1374959A/zh active Pending
- 2000-09-14 IL IL14872000A patent/IL148720A0/xx unknown
- 2000-09-14 GE GEAP20006413A patent/GEP20043223B/en unknown
- 2000-09-14 AT AT00962637T patent/ATE284399T1/de not_active IP Right Cessation
- 2000-09-14 YU YU19002A patent/YU19002A/sh unknown
- 2000-09-14 JP JP2001528171A patent/JP2004527448A/ja active Pending
- 2000-09-14 OA OA1200200074A patent/OA12022A/fr unknown
- 2000-09-14 DE DE60034713T patent/DE60034713T2/de not_active Expired - Fee Related
- 2000-09-14 EP EP04019136A patent/EP1484328B1/de not_active Expired - Lifetime
- 2000-09-15 TN TNTNSN00184A patent/TNSN00184A1/fr unknown
2002
- 2002-03-13 ZA ZA200202073A patent/ZA200202073B/en unknown
- 2002-03-13 NO NO20021253A patent/NO20021253L/no not_active Application Discontinuation
- 2002-03-14 MA MA26554A patent/MA26820A1/fr unknown
- 2002-03-15 BG BG106524A patent/BG106524A/xx unknown

Also Published As

Publication number	Publication date
CN1374959A (zh)	2002-10-16
MXPA02001979A (es)	2002-08-20
TNSN00184A1 (fr)	2005-11-10
HUP0204283A3 (en)	2004-07-28
GEP20043223B (en)	2004-04-26
EA200200374A1 (ru)	2002-10-31
JP2004527448A (ja)	2004-09-09
EP1218370A2 (de)	2002-07-03
BG106524A (en)	2003-01-31
BR0014060A (pt)	2002-05-21
PL354809A1 (en)	2004-02-23
NO20021253L (no)	2002-04-24
HUP0204283A2 (hu)	2003-04-28
ZA200202073B (en)	2003-08-27
DE60034713T2 (de)	2008-01-17
DE60034713D1 (de)	2007-06-14
DZ3195A1 (fr)	2001-04-12
NO20021253D0 (no)	2002-03-13
EP1484328A1 (de)	2004-12-08
FR2798656A1 (fr)	2001-03-23
HRP20020214A2 (en)	2005-04-30
KR20020038757A (ko)	2002-05-23
DE60016611D1 (de)	2005-01-13
OA12022A (fr)	2006-04-19
EE200200138A (et)	2003-06-16
EP1218370B1 (de)	2004-12-08
MA26820A1 (fr)	2004-12-20
CA2383836A1 (fr)	2001-04-12
CZ2002940A3 (cs)	2002-07-17
AU7429500A (en)	2001-05-10
IL148720A0 (en)	2002-09-12
EA005183B1 (ru)	2004-12-30
WO2001025227A2 (fr)	2001-04-12
DE60016611T2 (de)	2005-12-22
ATE284399T1 (de)	2004-12-15
WO2001025227A3 (fr)	2001-11-22
YU19002A (sh)	2005-06-10
EP1484328B1 (de)	2007-05-02
AP2002002459A0 (en)	2002-06-30
FR2798656B1 (fr)	2004-12-17

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