FI72317C - Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt. - Google Patents

Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt. Download PDF

Info

Publication number: FI72317C
Authority: FI; Finland
Prior art keywords: benzothiazine; dioxide; methyl; pyridyl; hydroxy
Prior art date: 1983-10-06

Application number

FI833628A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI833628A0 (fi

FI833628A7 (fi

FI72317B (fi

Inventor

Erkki Juhani Honkanen

Pekka Juhani Kairisalo

Aino Kyllikki Pippuri

Pentti Tapio Nore

Magnus Edvard Valdem Johansson

Matti Karhu

Irma Ritva Helena Kurimo

Original Assignee

Pfizer

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.)

1983-10-06

Filing date

1983-10-06

Publication date

1987-05-11

1983-10-06 Application filed by Pfizer filed Critical Pfizer

1983-10-06 Publication of FI833628A0 publication Critical patent/FI833628A0/fi

1983-10-06 Priority to FI833628A priority Critical patent/FI72317C/fi

1984-10-01 Priority to NO843949A priority patent/NO159275C/no

1984-10-02 Priority to DK471284A priority patent/DK154504C/da

1984-10-03 Priority to HU844649A priority patent/HU195493B/hu

1984-10-03 Priority to HU843746A priority patent/HU194559B/hu

1984-10-03 Priority to CS847493A priority patent/CS253593B2/cs

1984-10-04 Priority to PT79326A priority patent/PT79326B/pt

1984-10-04 Priority to YU1708/84A priority patent/YU43381B/xx

1984-10-04 Priority to IT22981/84A priority patent/IT1218850B/it

1984-10-05 Priority to ES536544A priority patent/ES8505937A1/es

1984-10-05 Priority to DD84268074A priority patent/DD224594A5/de

1984-10-05 Priority to CA000464861A priority patent/CA1246066A/en

1984-10-05 Priority to AT0316384A priority patent/AT387775B/de

1984-10-05 Priority to PL1984249918A priority patent/PL143957B1/pl

1984-10-05 Priority to SE8405002A priority patent/SE460789B/sv

1984-10-05 Priority to BE0/213782A priority patent/BE900758A/fr

1984-10-05 Priority to SU843805901A priority patent/SU1405703A3/ru

1985-04-07 Publication of FI833628A7 publication Critical patent/FI833628A7/fi

1985-12-09 Priority to ES85549709A priority patent/ES8606313A3/es

1986-08-27 Priority to YU1496/86A priority patent/YU43603B/xx

1987-01-30 Application granted granted Critical

1987-01-30 Publication of FI72317B publication Critical patent/FI72317B/fi

1987-05-11 Publication of FI72317C publication Critical patent/FI72317C/fi

1987-12-09 Priority to NO875130A priority patent/NO159088C/no

1989-01-24 Priority to SE8900248A priority patent/SE464411B/sv

Links

238000000034 method Methods 0.000 title claims description 25
JAPXKBYCCYOVDH-UHFFFAOYSA-N 2-methyl-1,1-dioxo-1$l^{6},2-benzothiazin-4-ol Chemical compound C1=CC=C2S(=O)(=O)N(C)C=C(O)C2=C1 JAPXKBYCCYOVDH-UHFFFAOYSA-N 0.000 title 1
239000003814 drug Substances 0.000 title 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 10
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
125000005905 mesyloxy group Chemical group 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 11
229960002702 piroxicam Drugs 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002253 acid Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
-1 methoxyethyl ester Chemical class 0.000 description 4
239000012453 solvate Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000009776 industrial production Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
ZYOCCCWHGRNSDO-UHFFFAOYSA-N 1,1,4-trioxo-2,3-dihydro-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)N)NS(=O)(=O)C2=C1 ZYOCCCWHGRNSDO-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical group C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
YBRHODCMROOROS-UHFFFAOYSA-N 2h-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2SNC(C(=O)O)=CC2=C1 YBRHODCMROOROS-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
XPSCEWSEWQROHI-UHFFFAOYSA-N CN(C(C)=O)C.CN1S(C2=C(C(=C1C(=O)O)OS(=O)(=O)C)C=CC=C2)(=O)=O Chemical compound CN(C(C)=O)C.CN1S(C2=C(C(=C1C(=O)O)OS(=O)(=O)C)C=CC=C2)(=O)=O XPSCEWSEWQROHI-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000003328 mesylation reaction Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

FI833628A 1983-10-06 1983-10-06 Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt. FI72317C (fi)

Priority Applications (21)

Application Number	Priority Date	Filing Date	Title
FI833628A FI72317C (fi)	1983-10-06	1983-10-06	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt.
NO843949A NO159275C (no)	1983-10-06	1984-10-01	Fremgangsmaate for fremstilling av 2-metyl-4-hydroksy-2h-1,2-benzotiazin-1,1-dioksyd-3-(n-2-pyridyl)-karboksamid (piroksikam).
DK471284A DK154504C (da)	1983-10-06	1984-10-02	Fremgangsmaade til fremstilling af benzotiazindioxyd samt mellemprodukt til anvendelse ved udoevelse af fremgangsmaaden
HU844649A HU195493B (en)	1983-10-06	1984-10-03	Process for producing new benzothiazine-dioxide-carboxylic acid derivative
HU843746A HU194559B (en)	1983-10-06	1984-10-03	New process for the production of curative benzothiazine-dioxide-derivatives
CS847493A CS253593B2 (en)	1983-10-06	1984-10-03	Method of pharmaceutically applicable 2-methyl-4-hydrox!-2h-1,2-benzothiazine-1,1-dioxide-3-(n-2-pyridyl)carboxamide production
PT79326A PT79326B (en)	1983-10-06	1984-10-04	Process for preparing a pharmaceutically usable benzothiazine dioxide and an intermediate for said process
YU1708/84A YU43381B (en)	1983-10-06	1984-10-04	Process for making pharmaceutically useful 2-methyl-4-hydroxy-2h-1,2-benzothiazine-1,1-dioxide-3-(n-2-pyridil)-carboxamide
IT22981/84A IT1218850B (it)	1983-10-06	1984-10-04	Procedimento per la preaparazione di biossido di benzotiazina farmaceuticamente utilizzabile e intermedio da usare nel procedimento
SU843805901A SU1405703A3 (ru)	1983-10-06	1984-10-05	Способ получени 2-метил-4-гидрокси-2Н-1,2-бензотиазин-1,1-диоксид-3-N-(2-пиридил)-карбоксамида
ES536544A ES8505937A1 (es)	1983-10-06	1984-10-05	Un metodo para la preparacion de una 2-metil-4-hidroxi-2h-1, 2-benzotiacin-1, 1-dioxido-3-(n-2-piridil)-carboxamida
CA000464861A CA1246066A (en)	1983-10-06	1984-10-05	Method for the preparation of a pharmaceutically usable benzothiazine dioxide, and an intermediate for use in the method
AT0316384A AT387775B (de)	1983-10-06	1984-10-05	Verfahren zur herstellung von piroxicam
PL1984249918A PL143957B1 (en)	1983-10-06	1984-10-05	Method of obtaining pharmaceutically useful benzothiasine dioxide
SE8405002A SE460789B (sv)	1983-10-06	1984-10-05	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-bensotiazin-1,1-dioxid-3-(n-2-pyridyl)-karboxamid
BE0/213782A BE900758A (fr)	1983-10-06	1984-10-05	Procede de preparation d'un benzothiadiazine dioxyde et intermediaire convenant a sa preparation.
DD84268074A DD224594A5 (de)	1983-10-06	1984-10-05	Verfahren zur herstellung eines pharmazeutisch verwendbaren benzothiazindioxids
ES85549709A ES8606313A3 (es)	1983-10-06	1985-12-09	Procedimiento de preparacion de 2-metil-4-hidroxi-2h-1, 2-benzotiazina-1,1-dioxido-3-(n-2-piridil)-carboxamida.
YU1496/86A YU43603B (en)	1983-10-06	1986-08-27	Process for making pharmaceutically usable 2-methyl-4-carboxy-4-mezyloxy-2h-1,2-benzothiazine-1,1-dioxide-3-n,n-dimethylacetamid solvates
NO875130A NO159088C (no)	1983-10-06	1987-12-09	Nytt benzotiazindioksyd-derivat.
SE8900248A SE464411B (sv)	1983-10-06	1989-01-24	Mellanprodukten 2-metyl-4-mesyloxi-2h-1,2-bensotiazin-1,1-dioxid-3-karboxylsyra eller ett solvat daerav med dimetylacetamid foer anvaendning vid framstaellning av en farmaceutiskt anvaendbar bensotiazin-dioxid

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI833628		1983-10-06
FI833628A FI72317C (fi)	1983-10-06	1983-10-06	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt.

Publications (4)

Publication Number	Publication Date
FI833628A0 FI833628A0 (fi)	1983-10-06
FI833628A7 FI833628A7 (fi)	1985-04-07
FI72317B FI72317B (fi)	1987-01-30
FI72317C true FI72317C (fi)	1987-05-11

Family

ID=8517867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI833628A FI72317C (fi)	1983-10-06	1983-10-06	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt.

Country Status (16)

Country	Link
AT (1)	AT387775B (cs)
BE (1)	BE900758A (cs)
CA (1)	CA1246066A (cs)
CS (1)	CS253593B2 (cs)
DD (1)	DD224594A5 (cs)
DK (1)	DK154504C (cs)
ES (1)	ES8505937A1 (cs)
FI (1)	FI72317C (cs)
HU (2)	HU194559B (cs)
IT (1)	IT1218850B (cs)
NO (1)	NO159275C (cs)
PL (1)	PL143957B1 (cs)
PT (1)	PT79326B (cs)
SE (2)	SE460789B (cs)
SU (1)	SU1405703A3 (cs)
YU (2)	YU43381B (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4289879A (en) *	1980-09-29	1981-09-15	Pfizer Inc.	Synthetic method and intermediate for piroxicam
JPH08270888A (ja) *	1995-03-30	1996-10-15	Nec Eng Ltd	断熱締結機構

1983
- 1983-10-06 FI FI833628A patent/FI72317C/fi not_active IP Right Cessation
1984
- 1984-10-01 NO NO843949A patent/NO159275C/no not_active IP Right Cessation
- 1984-10-02 DK DK471284A patent/DK154504C/da not_active IP Right Cessation
- 1984-10-03 HU HU843746A patent/HU194559B/hu unknown
- 1984-10-03 HU HU844649A patent/HU195493B/hu unknown
- 1984-10-03 CS CS847493A patent/CS253593B2/cs unknown
- 1984-10-04 YU YU1708/84A patent/YU43381B/xx unknown
- 1984-10-04 IT IT22981/84A patent/IT1218850B/it active
- 1984-10-04 PT PT79326A patent/PT79326B/pt not_active IP Right Cessation
- 1984-10-05 ES ES536544A patent/ES8505937A1/es not_active Expired
- 1984-10-05 CA CA000464861A patent/CA1246066A/en not_active Expired
- 1984-10-05 AT AT0316384A patent/AT387775B/de active
- 1984-10-05 SU SU843805901A patent/SU1405703A3/ru active
- 1984-10-05 BE BE0/213782A patent/BE900758A/fr not_active IP Right Cessation
- 1984-10-05 DD DD84268074A patent/DD224594A5/de not_active IP Right Cessation
- 1984-10-05 SE SE8405002A patent/SE460789B/sv not_active IP Right Cessation
- 1984-10-05 PL PL1984249918A patent/PL143957B1/pl unknown
1986
- 1986-08-27 YU YU1496/86A patent/YU43603B/xx unknown
1989
- 1989-01-24 SE SE8900248A patent/SE464411B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI833628A0 (fi)	1983-10-06
IT1218850B (it)	1990-04-24
ES536544A0 (es)	1985-07-01
CS253593B2 (en)	1987-11-12
ATA316384A (de)	1988-08-15
HU195493B (en)	1988-05-30
NO843949L (no)	1985-04-09
YU43381B (en)	1989-06-30
PL143957B1 (en)	1988-03-31
NO159275C (no)	1988-12-14
IT8422981A0 (it)	1984-10-04
BE900758A (fr)	1985-02-01
PL249918A1 (en)	1985-07-30
YU43603B (en)	1989-08-31
SE8900248L (sv)	1989-01-24
AT387775B (de)	1989-03-10
DK154504C (da)	1989-04-10
SE460789B (sv)	1989-11-20
FI833628A7 (fi)	1985-04-07
HU194559B (en)	1988-02-29
DK154504B (da)	1988-11-21
HUT37427A (en)	1985-12-28
PT79326B (en)	1986-09-08
SE8405002D0 (sv)	1984-10-05
SU1405703A3 (ru)	1988-06-23
PT79326A (en)	1984-11-01
NO159275B (no)	1988-09-05
CA1246066A (en)	1988-12-06
YU170884A (en)	1986-12-31
SE464411B (sv)	1991-04-22
SE8405002L (sv)	1985-04-07
ES8505937A1 (es)	1985-07-01
FI72317B (fi)	1987-01-30
DD224594A5 (de)	1985-07-10
SE8900248D0 (sv)	1989-01-24
YU149686A (en)	1986-12-31
DK471284D0 (da)	1984-10-02
DK471284A (da)	1985-04-07

Legal Events

Date	Code	Title	Description
2004-08-31	MA	Patent expired	Owner name: PFIZER INC.

Publication	Publication Date	Title
EP0425650B1 (en)	1995-08-09	Anti-inflammatory 4-aminophenol derivatives
WO2001044172A1 (en)	2001-06-21	Salicylamides as serine protease and factor xa inhibitors
FI72317C (fi)	1987-05-11	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt.
HUP0004855A2 (hu)	2001-06-28	Eljárás kinolinszármazékok előállítására és az eljárás intermedierjei
US4801590A (en)	1989-01-31	Pyrido(1,8)naphthyridinones, and their use as pharmaceuticals
CN108794396A (zh)	2018-11-13	4-氧代-2,3-二氢喹啉类化合物的氧化方法
Urban et al.	1996	A novel synthesis of the antipsychotic agent ziprasidone
HU187471B (en)	1986-01-28	Process for preparing n-acyl-triptamine derivatives and pharmaceutical compositions containing them as active agents
EP0481891B1 (en)	1995-02-08	Phenoxyacetic acid compounds, method for production thereof, and pharmaceutical preparations containing same
US6573384B1 (en)	2003-06-03	Process for production of indole derivatives and intermediates therefor
JPH0324069A (ja)	1991-02-01	ベンゾ〔ｂ〕フラン誘導体
KR100424341B1 (ko)	2004-03-24	1-메틸인다졸-3-카르복실산의 제조방법
PL174102B1 (pl)	1998-06-30	Nowe izobutylopodstawione metanosulfonyloamidy kwasów chinolilometoksyfenylo-cykloalkilooctowych
KR100247607B1 (ko)	2000-04-01	3,4,5,6-테트라히드로프탈이미드 유도체의 제조방법
HU201315B (en)	1990-10-28	Process for the production of benzimidazole-derivatives
US5476940A (en)	1995-12-19	3-substituted quinoline-5-carboxylic acids
Rádl	1994	Synthesis of 3-Amino-and 3-Acylamino-1-cyclopropylquinolin-4 (1H)-ones
JPS61158962A (ja)	1986-07-18	１，４−ジヒドロピリジン誘導体の製造法
KR100276974B1 (ko)	2001-01-15	아세클로페낙의 제조방법
KR0139260B1 (ko)	1998-05-15	고리화된 이미다졸을 가지는 벤즈이미다졸 유도체
JPH0489452A (ja)	1992-03-23	環式化合物
JPS602311B2 (ja)	1985-01-21	ペニシリンエステルの製造法
JPS62195366A (ja)	1987-08-28	５−ヒドラジノ−１ｈ−ピラゾ−ル系化合物
HU183207B (en)	1984-04-28	Process for preparing apovincaminic acid esters
FR2562540A1 (fr)	1985-10-11	Nouvelles dihydropyridines, leur procede de preparation et leur application notamment a l'obtention de pyridines