SE445917B - Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition - Google Patents

Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition

Info

Publication number: SE445917B
Authority: SE; Sweden
Prior art keywords: group; compound; formula; carboxylic acid; quinolizine
Prior art date: 1979-10-11

Application number

SE8007133A

Other languages

English (en)

Swedish (sv)

Other versions

SE8007133L (sv

Inventor

H Ishikawa

F Tabusa

K Nakagawa

Original Assignee

Otsuka Pharma Co Ltd

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.)

1979-10-11

Filing date

1980-10-10

Publication date

1986-07-28

1980-10-10 Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd

1981-04-12 Publication of SE8007133L publication Critical patent/SE8007133L/xx

1986-07-28 Publication of SE445917B publication Critical patent/SE445917B/sv

Links

239000000203 mixture Substances 0.000 title claims description 49
IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 title description 2
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 161
-1 quinolizine-2-carboxylic acid compound Chemical class 0.000 claims description 79
125000005843 halogen group Chemical group 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
230000000845 anti-microbial effect Effects 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 6
239000004599 antimicrobial Substances 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
125000005270 trialkylamine group Chemical group 0.000 claims description 5
150000001449 anionic compounds Chemical class 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
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125000005208 trialkylammonium group Chemical group 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 55
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
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229920002472 Starch Polymers 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
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235000019698 starch Nutrition 0.000 description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
229940124597 therapeutic agent Drugs 0.000 description 5
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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239000002202 Polyethylene glycol Substances 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 4
229960000210 nalidixic acid Drugs 0.000 description 4
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239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-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
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
150000003512 tertiary amines Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- 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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)
Nitrogen Condensed Heterocyclic Rings (AREA)

SE8007133A 1979-10-11 1980-10-10 Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition SE445917B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP54131630A JPS6019910B2 (ja)	1979-10-11	1979-10-11	ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体及びその製造法

Publications (2)

Publication Number	Publication Date
SE8007133L SE8007133L (sv)	1981-04-12
SE445917B true SE445917B (sv)	1986-07-28

Family

ID=15062532

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8007133A SE445917B (sv)	1979-10-11	1980-10-10	Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition

Country Status (12)

Country	Link
JP (1)	JPS6019910B2 (it)
AU (1)	AU536230B2 (it)
BE (1)	BE885605A (it)
CA (1)	CA1156232A (it)
CH (1)	CH644859A5 (it)
DE (1)	DE3037103A1 (it)
ES (1)	ES496312A0 (it)
FR (1)	FR2467205A1 (it)
GB (1)	GB2062627B (it)
IT (1)	IT1143997B (it)
NL (1)	NL187020C (it)
SE (1)	SE445917B (it)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57176987A (en) *	1981-04-24	1982-10-30	Otsuka Pharmaceut Co Ltd	Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative
NO156828C (no) *	1980-11-10	1987-12-02	Otsuka Pharma Co Ltd	Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser.
US4400386A (en) *	1981-11-06	1983-08-23	Riker Laboratories, Inc.	Antimicrobial derivatives of 8-amino and 8-aminomethyl benzo(ij)quinolizine
US4472406A (en) *	1982-11-12	1984-09-18	Riker Laboratories, Inc.	Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives
JPS59137482A (ja) *	1983-01-26	1984-08-07	Otsuka Pharmaceut Co Ltd	ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体
JPS59155381A (ja) *	1983-02-22	1984-09-04	Kyorin Pharmaceut Co Ltd	ベンゾキノリジンカルボン酸誘導体及びその製造法
DE3333719A1 (de) *	1983-09-17	1985-04-04	Bayer Ag	Loesungen milchsaurer salze von piperazinylchinolon- und piperazinyl-azachinoloncarbonsaeuren
JPS60161987A (ja) *	1984-01-31	1985-08-23	Otsuka Pharmaceut Co Ltd	ベンゾヘテロ環誘導体
DE3517709A1 (de) *	1985-01-05	1986-07-10	Bayer Ag	Basische zubereitungen von chinoloncarbonsaeuren
AU585981B2 (en) *	1985-05-24	1989-06-29	Tokyo Tanabe Company Limited	Benzo (IJ) quinolizine-2-carboxylic acid derivatives, the salts and their hydrates, pharmaceutical compositions thereof, and processes for preparing the same
DE3741026A1 (de) *	1987-12-03	1989-06-15	Muetek Laser Und Opto Elektron	Verfahren und system zur (spuren-) gasanalyse

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE793524A (fr) *	1971-12-30	1973-06-29	Riker Laboratories Inc	Acides benzoquinolizine-carboxyliques et leurs derives
JPS6034957B2 (ja) *	1978-04-12	1985-08-12	大塚製薬株式会社	ペニシラン酸誘導体

1979
- 1979-10-11 JP JP54131630A patent/JPS6019910B2/ja not_active Expired
1980
- 1980-10-01 DE DE19803037103 patent/DE3037103A1/de active Granted
- 1980-10-06 CH CH743580A patent/CH644859A5/de not_active IP Right Cessation
- 1980-10-09 CA CA000362012A patent/CA1156232A/en not_active Expired
- 1980-10-09 BE BE0/202389A patent/BE885605A/fr not_active IP Right Cessation
- 1980-10-09 AU AU63090/80A patent/AU536230B2/en not_active Ceased
- 1980-10-09 IT IT49851/80A patent/IT1143997B/it active
- 1980-10-10 NL NLAANVRAGE8005613,A patent/NL187020C/xx not_active IP Right Cessation
- 1980-10-10 SE SE8007133A patent/SE445917B/sv not_active IP Right Cessation
- 1980-10-10 FR FR8021722A patent/FR2467205A1/fr active Granted
- 1980-10-10 GB GB8032782A patent/GB2062627B/en not_active Expired
- 1980-10-11 ES ES496312A patent/ES496312A0/es active Granted

Also Published As

Publication number	Publication date
AU536230B2 (en)	1984-05-03
FR2467205A1 (fr)	1981-04-17
JPS5655389A (en)	1981-05-15
ES8106903A1 (es)	1981-10-01
IT8049851A0 (it)	1980-10-09
CH644859A5 (de)	1984-08-31
ES496312A0 (es)	1981-10-01
FR2467205B1 (it)	1983-10-07
IT1143997B (it)	1986-10-29
CA1156232A (en)	1983-11-01
JPS6019910B2 (ja)	1985-05-18
AU6309080A (en)	1981-04-16
BE885605A (fr)	1981-02-02
SE8007133L (sv)	1981-04-12
GB2062627B (en)	1983-12-07
NL8005613A (nl)	1981-04-14
NL187020B (nl)	1990-12-03
NL187020C (nl)	1991-05-01
GB2062627A (en)	1981-05-28
DE3037103A1 (de)	1981-05-07
DE3037103C2 (it)	1989-06-15

Publication	Publication Date	Title
US4399134A (en)	1983-08-16	Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions
US4416884A (en)	1983-11-22	Piperazinylbenzoheterocyclic compounds
US4359578A (en)	1982-11-16	Naphthyridine derivatives and salts thereof useful as antibacterial agents
CA1204748A (en)	1986-05-20	Benzo-heterocyclic compounds
US4341784A (en)	1982-07-27	Naphthyridine derivatives
IE54898B1 (en)	1990-03-14	New quinolone compounds and preparation thereof
SE445917B (sv)	1986-07-28	Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition
CA1153374A (en)	1983-09-06	Piperazinylbenzoheterocyclic compounds
JPH0141127B2 (it)	1989-09-04
US4720495A (en)	1988-01-19	Benzo[ij]quinolizine-2-carboxylic acids useful for treating bacterial infection
US4317820A (en)	1982-03-02	β-Lactam series compound and antibacterial pharmaceutical composition containing the same
US4497816A (en)	1985-02-05	7-(4-Pyridyl)-1,8-naphthyridine derivatives and their antibacterial compositions
JPS6310684B2 (it)	1988-03-08
JPS622598B2 (it)	1987-01-20
DK160306B (da)	1991-02-25	Analogifremgangsmaade til fremstilling af piperazinylbenzoheterocycliske forbindelser eller farmaceutisk acceptable salte deraf
KR830001943B1 (ko)	1983-09-26	피페라지닐 벤조 복소환 화합물의 제조방법
SE436280B (sv)	1984-11-26	Piperazinylbensoheterocykliska foreningar av antimikrobiellt preparat derav
KR820001200B1 (ko)	1982-07-01	β-락탐 유도체의 제조방법
US4293694A (en)	1981-10-06	Pyrido[3,2,1-jk]carbazols
CS235545B2 (cs)	1985-05-15	Způsob přípravy derivátů 1-ethyl nebo vinyl-6-halogen-1,4-dihydro-4- oxo-7-/1 -piperazinyl/-!,8-nafthyridinu

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