PH26185A - (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid - Google Patents

(S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid Download PDF

Info

Publication number: PH26185A
Authority: PH; Philippines
Prior art keywords: amino; dihydro; fluoro; naphthyridine; carboxylic acid
Prior art date: 1989-03-28

Application number

PH40268A

Other languages

English (en)

Inventor

Joseph-Lambert Company

Original Assignee

Warner Lambert Co

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.)

1989-03-28

Filing date

1990-03-27

Publication date

1992-03-18

1990-03-27 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1992-03-18 Publication of PH26185A publication Critical patent/PH26185A/en

Links

MUKSDTOOLRNSIO-QMMMGPOBSA-N 7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 MUKSDTOOLRNSIO-QMMMGPOBSA-N 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 47
150000003839 salts Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 5
208000022362 bacterial infectious disease Diseases 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
125000005907 alkyl ester group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
238000009472 formulation Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 18
-1 p-methoxybenzyloxycarbonyl Chemical group 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 10
239000002585 base Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012458 free base Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000002674 ointment Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YDBGWEQJELDERH-BYPYZUCNSA-N (3S)-3-azidopyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CC[C@H](N=[N+]=[N-])C1 YDBGWEQJELDERH-BYPYZUCNSA-N 0.000 description 2
MKSTXMDSWOHKOR-SCSAIBSYSA-N (3r)-3-aminopyrrolidine-1-carboxylic acid Chemical compound N[C@@H]1CCN(C(O)=O)C1 MKSTXMDSWOHKOR-SCSAIBSYSA-N 0.000 description 2
ZVPWXQHLRXNEAA-LLVKDONJSA-N 1-cyclopropyl-6-fluoro-7-[(3r)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1[C@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 ZVPWXQHLRXNEAA-LLVKDONJSA-N 0.000 description 2
OXNZWNNMJBOZQO-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OXNZWNNMJBOZQO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000012052 hydrophilic carrier Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
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235000010981 methylcellulose Nutrition 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
DQQJBEAXSOOCPG-SSDOTTSWSA-N tert-butyl n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCNC1 DQQJBEAXSOOCPG-SSDOTTSWSA-N 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
YDBGWEQJELDERH-SCSAIBSYSA-N (3R)-3-azidopyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CC[C@@H](N=[N+]=[N-])C1 YDBGWEQJELDERH-SCSAIBSYSA-N 0.000 description 1
YZGYKWJZOBALKZ-SCSAIBSYSA-N (3r)-3-hydroxypyrrolidine-1-carboxylic acid Chemical compound O[C@@H]1CCN(C(O)=O)C1 YZGYKWJZOBALKZ-SCSAIBSYSA-N 0.000 description 1
JHHZLHWJQPUNKB-SCSAIBSYSA-N (3r)-pyrrolidin-3-ol Chemical compound O[C@@H]1CCNC1 JHHZLHWJQPUNKB-SCSAIBSYSA-N 0.000 description 1
QPMSJEFZULFYTB-PGMHMLKASA-N (3r)-pyrrolidin-3-ol;hydrochloride Chemical compound Cl.O[C@@H]1CCNC1 QPMSJEFZULFYTB-PGMHMLKASA-N 0.000 description 1
JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 1
QPMSJEFZULFYTB-WCCKRBBISA-N (3s)-pyrrolidin-3-ol;hydrochloride Chemical compound Cl.O[C@H]1CCNC1 QPMSJEFZULFYTB-WCCKRBBISA-N 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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239000002202 Polyethylene glycol Substances 0.000 description 1
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HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
MBLJFGOKYTZKMH-LLVKDONJSA-N benzyl (3r)-3-hydroxypyrrolidine-1-carboxylate Chemical compound C1[C@H](O)CCN1C(=O)OCC1=CC=CC=C1 MBLJFGOKYTZKMH-LLVKDONJSA-N 0.000 description 1
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ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
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239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007430 reference method Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000006208 topical dosage form Substances 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000001974 tryptic soy broth Substances 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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

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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PH40268A 1989-03-28 1990-03-27 (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid PH26185A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/329,461 US4916141A (en)	1989-03-28	1989-03-28	(S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Publications (1)

Publication Number	Publication Date
PH26185A true PH26185A (en)	1992-03-18

Family

ID=23285509

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH40268A PH26185A (en)	1989-03-28	1990-03-27	(S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Country Status (12)

Country	Link
US (1)	US4916141A (sv)
EP (1)	EP0394685A3 (sv)
JP (1)	JP2948857B2 (sv)
KR (1)	KR900014382A (sv)
AU (1)	AU617974B2 (sv)
CA (1)	CA2013136C (sv)
FI (1)	FI94640C (sv)
NO (1)	NO175369C (sv)
NZ (1)	NZ233087A (sv)
PH (1)	PH26185A (sv)
PT (1)	PT93571B (sv)
ZA (1)	ZA902356B (sv)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5057523A (en) *	1988-09-22	1991-10-15	Abbott Laboratories	Dipeptide quinolone derivatives
US5057520A (en) *	1989-03-24	1991-10-15	Abbott Laboratories	7-(peptidylpyrolidinyl)naphthyridine antibacterial compounds
US5177217A (en) *	1992-04-27	1993-01-05	Warner-Lambert Company	Process for the manufacture of (S)-3-amino-1-substituted-pyrrolidines
US5290794A (en) *	1992-10-27	1994-03-01	Warner Lambert Co.	Soluble calcium lactate antibacterial complexes as non-irritating parenteral forms
US5977381A (en) *	1998-01-12	1999-11-02	Hoffmann-La Roche Inc.	Process for making 3-amino-pyrolidine derivatives
KR100295740B1 (ko)	1998-09-17	2001-11-05	박영구	N-치환된-하이드록시고리화알킬아민유도체의제조방법
ATE338747T1 (de) *	2002-08-01	2006-09-15	Basilea Pharmaceutica Ag	Verfahren zur herstellung von aminopyrrolidinderivaten
KR100939347B1 (ko) *	2005-07-20	2010-01-29	(주)카이로드	광학적으로 순수한 (ｓ)-3-히드록시 피롤리딘의 제조방법
WO2008013130A1 (fr)	2006-07-28	2008-01-31	Kaneka Corporation	Méthode de production d'un composé 3-amino-azoté optiquement actif
EP2361244B1 (en)	2008-11-24	2013-07-10	Council of Scientific & Industrial Research	A process for the preparation of optically active n-benzyl-3 hydroxypyrrolidines
EP4382529A1 (en)	2022-12-07	2024-06-12	Bayer Consumer Care AG	A process for preparing pure (3s)-pyrrolidin-3-ol and pure (3s)-pyrrolidin-3-ol hydrochloride

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CS274601B2 (en) *	1983-07-27	1991-09-15	Dainippon Pharmaceutical Co	Method of 1,8-naphthyridine derivative production
ZA877471B (en) *	1986-10-08	1988-04-05	Bristol-Myers Company	1-tertiary-alkyl-substituted naphthyridine-and quinoline-carboxylic acid antibacterial agents
US4851418A (en) *	1987-08-21	1989-07-25	Warner-Lambert Company	Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent
AU5123690A (en) *	1989-03-13	1990-09-13	Bristol-Myers Squibb Company	5-substituted-1,4-dihydro-4-oxo-nephthyridine-3-carboxylate antibacterial agents

1989
- 1989-03-28 US US07/329,461 patent/US4916141A/en not_active Expired - Lifetime
1990
- 1990-03-26 FI FI901505A patent/FI94640C/sv not_active IP Right Cessation
- 1990-03-26 AU AU52197/90A patent/AU617974B2/en not_active Ceased
- 1990-03-26 NZ NZ233087A patent/NZ233087A/en unknown
- 1990-03-27 NO NO901391A patent/NO175369C/no not_active IP Right Cessation
- 1990-03-27 CA CA002013136A patent/CA2013136C/en not_active Expired - Fee Related
- 1990-03-27 EP EP19900105827 patent/EP0394685A3/en not_active Withdrawn
- 1990-03-27 ZA ZA902356A patent/ZA902356B/xx unknown
- 1990-03-27 PH PH40268A patent/PH26185A/en unknown
- 1990-03-27 PT PT93571A patent/PT93571B/pt not_active IP Right Cessation
- 1990-03-27 JP JP2075809A patent/JP2948857B2/ja not_active Expired - Fee Related
- 1990-03-27 KR KR1019900004097A patent/KR900014382A/ko not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU617974B2 (en)	1991-12-05
EP0394685A2 (en)	1990-10-31
FI94640B (sv)	1995-06-30
US4916141A (en)	1990-04-10
PT93571A (pt)	1990-11-07
JPH02289568A (ja)	1990-11-29
PT93571B (pt)	1996-08-30
JP2948857B2 (ja)	1999-09-13
ZA902356B (en)	1991-11-27
NO175369C (no)	1994-10-05
NO901391L (no)	1990-10-01
FI901505A0 (sv)	1990-03-26
EP0394685A3 (en)	1991-09-25
CA2013136C (en)	1998-09-15
AU5219790A (en)	1990-10-04
NO901391D0 (no)	1990-03-27
NZ233087A (en)	1991-07-26
CA2013136A1 (en)	1990-09-28
KR900014382A (ko)	1990-10-23
NO175369B (no)	1994-06-27
FI94640C (sv)	1995-10-10

Publication	Publication Date	Title
EP0326891B1 (en)	1994-08-03	Antibacterial agents
US4851418A (en)	1989-07-25	Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent
US4771055A (en)	1988-09-13	7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-quinoline-carboxylic acids
US4735949A (en)	1988-04-05	Disubstituted-7-pyrrolidinonaphthyridine antibacterial agents
US4840956A (en)	1989-06-20	Novel disubstituted-7-pyrrolidinoquinoline antibacterial agents
CA2013136C (en)	1998-09-15	(s)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
RU2100351C1 (ru)	1997-12-27	Производные пиридонкарбоновой кислоты и композиция на их основе
KR100531967B1 (ko)	2005-11-30	트리사이클릭 아민 유도체, 이를 포함하는 항균제 및 퀴놀론 화합물의 제조방법
US4668680A (en)	1987-05-26	5-amino-6,8-difluoroquinolones as antibacterial agents
US4617308A (en)	1986-10-14	7-substituted amino-1-aryl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and derivatives thereof as antibacterial agents
US5157128A (en)	1992-10-20	Certain optically active substituted α,α-dialkyl-pyrrolidine-3-methamines useful as intermediates
US5072001A (en)	1991-12-10	Certain optically active substituted 3-pyrraidine acetic acid derivatives useful as intermediates
US4923879A (en)	1990-05-08	1,8-Naphthyridines and their use as antibacterial agents
JPH02290870A (ja)	1990-11-30	対掌体的に純粋な７‐（３‐アミノ‐１‐ピロリジニル）‐キノロン‐および‐ナフチリドンカルボン酸
EP0812838B1 (en)	2002-05-02	Pyridonecarboxylic acid derivative substituted by bicyclic amino group, ester thereof, salt thereof, and bicyclic amine as intermediate therefor
US5364861A (en)	1994-11-15	Optical isomers of 7-[3-(1,1-dialkylmethyl-1-amino-1-pyrrolidinyl]-quinolones and naphthyridones as antibacterial agents
US4962108A (en)	1990-10-09	Antibacterial quinoline compounds
US4968799A (en)	1990-11-06	Antibacterial agents
US4992546A (en)	1991-02-12	Process for preparing 6,8-diazabicyclo[3.2.2]nonane derivatives
KR100359151B1 (ko)	2003-01-24	2환성 아미노기로 치환된 피리돈카르복실산 유도체, 그의 에스테르 및 그의 염 및 이들의 중간체인 2환성 아민
JP4619952B2 (ja)	2011-01-26	８−シアノキノロンカルボン酸誘導体