NL8003832A - Werkwijze voor het bereiden van een basische oplossing van 5-mercaptotetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-broom-tetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-mercapto-tetrazolyl- -1-azijnzuur. - Google Patents

Werkwijze voor het bereiden van een basische oplossing van 5-mercaptotetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-broom-tetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-mercapto-tetrazolyl- -1-azijnzuur. Download PDF

Info

Publication number: NL8003832A
Authority: NL; Netherlands
Prior art keywords: acetic acid; tetrazolyl; bromotetrazolyl; solution; preparing
Prior art date: 1979-07-05

Application number

NL8003832A

Other languages

English (en)

Dutch (nl)

Original Assignee

Bristol Myers 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.)

1979-07-05

Filing date

1980-07-02

Publication date

1981-01-07

1980-07-02 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1981-01-07 Publication of NL8003832A publication Critical patent/NL8003832A/nl

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 167
239000003637 basic solution Substances 0.000 title claims description 30
238000004519 manufacturing process Methods 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 12
-1 5-MERCAPTO-TETRAZOLYL Chemical class 0.000 title description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 36
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 36
239000000243 solution Substances 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 15
239000007787 solid Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 9
238000003756 stirring Methods 0.000 claims description 9
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
229960000583 acetic acid Drugs 0.000 description 53
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003536 tetrazoles Chemical class 0.000 description 3
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
SLAYUXIURFNXPG-CRAIPNDOSA-N ceforanide Chemical compound NCC1=CC=CC=C1CC(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)CC(O)=O)CS[C@@H]21 SLAYUXIURFNXPG-CRAIPNDOSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
IYPXPGSELZFFMI-UHFFFAOYSA-N 1-phenyltetrazole Chemical compound C1=NN=NN1C1=CC=CC=C1 IYPXPGSELZFFMI-UHFFFAOYSA-N 0.000 description 1
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
OKBYPPLWGIVLOC-UHFFFAOYSA-N 5-bromo-1-phenyltetrazole Chemical compound BrC1=NN=NN1C1=CC=CC=C1 OKBYPPLWGIVLOC-UHFFFAOYSA-N 0.000 description 1
XBWRULFISNEVBP-UHFFFAOYSA-N 5-methyl-1,2-dihydropyrazole-3-thione Chemical compound CC1=CC(S)=NN1 XBWRULFISNEVBP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
229960004292 ceforanide Drugs 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000012087 reference standard solution Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000004905 tetrazines Chemical class 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

NL8003832A 1979-07-05 1980-07-02 Werkwijze voor het bereiden van een basische oplossing van 5-mercaptotetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-broom-tetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-mercapto-tetrazolyl- -1-azijnzuur. NL8003832A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/054,743 US4374994A (en)	1979-07-05	1979-07-05	Process for preparation of 5-mercaptotetrazolyl-1-acetic acid
US5474379		1979-07-05

Publications (1)

Publication Number	Publication Date
NL8003832A true NL8003832A (nl)	1981-01-07

Family

ID=21993217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8003832A NL8003832A (nl)	1979-07-05	1980-07-02	Werkwijze voor het bereiden van een basische oplossing van 5-mercaptotetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-broom-tetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-mercapto-tetrazolyl- -1-azijnzuur.

Country Status (11)

Country	Link
US (1)	US4374994A (da)
JP (1)	JPS5610178A (da)
CA (1)	CA1145757A (da)
CH (2)	CH644852A5 (da)
DK (3)	DK157298C (da)
FI (1)	FI66855C (da)
GR (1)	GR69331B (da)
IT (2)	IT1145663B (da)
NL (1)	NL8003832A (da)
SE (2)	SE448463B (da)
YU (1)	YU42340B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110627736B (zh) *	2019-09-26	2020-11-06	江苏阿尔法药业有限公司	一种1-苯基-5-羟基四氮唑的回收利用方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4297489A (en) *	1974-09-03	1981-10-27	Bristol-Myers Company	7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids

1979
- 1979-07-05 US US06/054,743 patent/US4374994A/en not_active Expired - Lifetime
1980
- 1980-05-21 CA CA000352344A patent/CA1145757A/en not_active Expired
- 1980-05-28 GR GR62070A patent/GR69331B/el unknown
- 1980-06-06 YU YU1513/80A patent/YU42340B/xx unknown
- 1980-06-26 JP JP8599580A patent/JPS5610178A/ja active Granted
- 1980-06-27 IT IT49102/80A patent/IT1145663B/it active
- 1980-06-27 IT IT49101/80A patent/IT1145662B/it active
- 1980-07-02 FI FI802127A patent/FI66855C/fi not_active IP Right Cessation
- 1980-07-02 NL NL8003832A patent/NL8003832A/nl not_active Application Discontinuation
- 1980-07-04 DK DK291480A patent/DK157298C/da not_active IP Right Cessation
- 1980-07-04 SE SE8004981A patent/SE448463B/sv not_active IP Right Cessation
- 1980-07-04 CH CH517180A patent/CH644852A5/de not_active IP Right Cessation
1984
- 1984-02-29 CH CH987/84A patent/CH648026A5/de not_active IP Right Cessation
- 1984-11-16 SE SE8405750A patent/SE454694B/sv not_active IP Right Cessation
1986
- 1986-01-10 DK DK011886A patent/DK160493C/da not_active IP Right Cessation
- 1986-01-10 DK DK011986A patent/DK160494C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT8049102A0 (it)	1980-06-27
GR69331B (da)	1982-05-17
DK160494B (da)	1991-03-18
SE8004981L (sv)	1981-01-06
SE454694B (sv)	1988-05-24
YU42340B (en)	1988-08-31
YU151380A (en)	1983-02-28
US4374994A (en)	1983-02-22
DK160494C (da)	1991-08-26
DK160493C (da)	1991-08-26
DK11886A (da)	1986-01-10
DK157298C (da)	1990-05-07
JPH0337550B2 (da)	1991-06-05
CH644852A5 (de)	1984-08-31
DK160493B (da)	1991-03-18
DK157298B (da)	1989-12-04
FI66855B (fi)	1984-08-31
IT1145663B (it)	1986-11-05
DK11886D0 (da)	1986-01-10
FI66855C (fi)	1984-12-10
DK291480A (da)	1981-01-06
SE8405750L (sv)	1984-11-16
CH648026A5 (de)	1985-02-28
JPS5610178A (en)	1981-02-02
DK11986D0 (da)	1986-01-10
FI802127A7 (fi)	1981-01-06
SE448463B (sv)	1987-02-23
DK11986A (da)	1986-01-10
CA1145757A (en)	1983-05-03
IT8049101A0 (it)	1980-06-27
SE8405750D0 (sv)	1984-11-16
IT1145662B (it)	1986-11-05

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-08-03	BA	A request for search or an international-type search has been filed
1988-01-04	BB	A search report has been drawn up
1988-06-01	BC	A request for examination has been filed
1990-05-16	DNT	Communications of changes of names of applicants whose applications have been laid open to public inspection	Free format text: BRISTOL-MYERS SQUIBB COMPANY
1997-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0354412A2 (de)	1990-02-14	Verfahren zur Herstellung von hochreinem Ebselen
Roblin Jr et al.	1942	Studies in Chemotherapy. IV. Sulfanilamidopyrimidines1
US3316266A (en)	1967-04-25	3-aminopyrazinoic acid derivatives and process for their preparation
NL8003832A (nl)	1981-01-07	Werkwijze voor het bereiden van een basische oplossing van 5-mercaptotetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-broom-tetrazolyl-1-azijnzuur; werkwijze voor het bereiden van 5-mercapto-tetrazolyl- -1-azijnzuur.
ALDOUS et al.	1960	Synthesis of Diaryloxazoles1-3
KR0146349B1 (ko)	1998-08-17	5-아미노-1,2,4-트리아졸-3-설폰아미드의 제조방법
US3474135A (en)	1969-10-21	N-(omega-aminoalkylene)-aminoalkyl sulfonic acids
JP2879164B2 (ja)	1999-04-05	置換２―シアノイミダゾール系化合物の製造方法
US3689502A (en)	1972-09-05	Preparation of n-(2-alkylthioethyl) nitroimidazoles
US3997537A (en)	1976-12-14	Process of preparing 2-amino-4-hydroxy-5(and/or 6)-alkyl substituted pyrimidines
US3197477A (en)	1965-07-27	Allylhydantoins
US2570392A (en)	1951-10-09	Halogenation of substituted
RU2067573C1 (ru)	1996-10-10	1,4-диароилтиосемикарбазиды, обладающие диуретической активностью
SU437764A1 (ru)	1974-07-30	Способ получени 5 (4)-тиопроизводных имидазола
Heath et al.	1951	491. 2-Mercaptoglyoxalines. Part IV. Bromination with N-bromosuccinimide. The Reimer–Tiemann reaction
KR830001325B1 (ko)	1983-07-09	비스페놀 술폰 유도체의 제조방법
JP3006875B2 (ja)	2000-02-07	４―（イミダゾリル―２’）―イミダゾール化合物
US3063997A (en)	1962-11-13	Process for preparing i
KR810000982B1 (ko)	1981-08-25	세팔로스포린 유도체의 제조방법
KR810000198B1 (ko)	1981-03-12	티크리나펜((ticrynafen))의 제조방법
KR810001135B1 (ko)	1981-09-20	탈암피실린 염산염의 제조방법
CS212286B2 (en)	1982-03-26	Method of making the molecular compound of betha-diethylaminothylamide of the p- chlorphenoxyvinegar acid with the 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidine
KR830002897B1 (ko)	1983-12-30	세펨계 항생물질 유도체의 제조방법
SU761465A1 (ru)	1980-09-07	Способ получения производных 5-(\|,2,4триазол ил-1 )-1,2,4-триазола
JPS5936977B2 (ja)	1984-09-06	４，４′−ビスフェノ−ルスルホン誘導体の製造方法