CA1088063A - Derivatives of thiazolo-[3,2-a]pyrimidin-7-one and thiadiazolo-[3,2-a]pyrimidin-7-one - Google Patents

Derivatives of thiazolo-[3,2-a]pyrimidin-7-one and thiadiazolo-[3,2-a]pyrimidin-7-one

Info

Publication number: CA1088063A
Authority: CA; Canada
Prior art keywords: carbon atoms; formula; compounds; alkyl; radical
Prior art date: 1976-06-04
Legal status (The legal status 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 status listed.): Expired

Application number

CA278,986A

Other languages

English (en)

French (fr)

Inventor

Siegfried Herrling

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gruenenthal GmbH

Original Assignee

Gruenenthal GmbH

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.)

1976-06-04

Filing date

1977-05-24

Publication date

1980-10-21

1977-05-24 Application filed by Gruenenthal GmbH filed Critical Gruenenthal GmbH

1980-10-21 Application granted granted Critical

1980-10-21 Publication of CA1088063A publication Critical patent/CA1088063A/en

Status Expired legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
150000001875 compounds Chemical class 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
150000001768 cations Chemical class 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract 6
239000000126 substance Substances 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
-1 acetylene dicarboxylic acid ester Chemical class 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 claims description 6
150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000000375 suspending agent Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims 3
238000006460 hydrolysis reaction Methods 0.000 claims 3
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 5
230000009385 viral infection Effects 0.000 abstract description 4
210000000987 immune system Anatomy 0.000 abstract description 2
125000004076 pyridyl group Chemical group 0.000 abstract description 2
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical group 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
230000008018 melting Effects 0.000 description 15
238000002844 melting Methods 0.000 description 15
239000000243 solution Substances 0.000 description 14
238000000354 decomposition reaction Methods 0.000 description 13
STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 13
241001465754 Metazoa Species 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229940093499 ethyl acetate Drugs 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
210000004027 cell Anatomy 0.000 description 8
206010057249 Phagocytosis Diseases 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008782 phagocytosis Effects 0.000 description 7
239000000155 melt Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
210000003743 erythrocyte Anatomy 0.000 description 4
210000002540 macrophage Anatomy 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000006143 cell culture medium Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000004816 latex Substances 0.000 description 3
229920000126 latex Polymers 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
210000000683 abdominal cavity Anatomy 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
210000003024 peritoneal macrophage Anatomy 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QNLNRENPKAQTMJ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(N)=N1 QNLNRENPKAQTMJ-UHFFFAOYSA-N 0.000 description 1
PYSJLPAOBIGQPK-UHFFFAOYSA-N 4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1 PYSJLPAOBIGQPK-UHFFFAOYSA-N 0.000 description 1
DJSKNOBOTVECTH-UHFFFAOYSA-N 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(N)=NN=2)=C1 DJSKNOBOTVECTH-UHFFFAOYSA-N 0.000 description 1
BQOCMHOWHOMIMJ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN=C(N)S1 BQOCMHOWHOMIMJ-UHFFFAOYSA-N 0.000 description 1
HKTCSEFOSVTSQV-UHFFFAOYSA-N 5-benzyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC=CC=C1 HKTCSEFOSVTSQV-UHFFFAOYSA-N 0.000 description 1
HTXQOROHFFYFMC-UHFFFAOYSA-N 5-methyl-4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1C HTXQOROHFFYFMC-UHFFFAOYSA-N 0.000 description 1
UHZHEOAEJRHUBW-UHFFFAOYSA-N 5-phenyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC=C1 UHZHEOAEJRHUBW-UHFFFAOYSA-N 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
108060003951 Immunoglobulin Proteins 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
241001529936 Murinae Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241000700605 Viruses Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
244000309466 calf Species 0.000 description 1
238000006482 condensation reaction 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
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
YOQQIZVZVMTRKZ-UHFFFAOYSA-N ethyl 2,3-dimethyl-7-oxo-[1,3]thiazolo[3,2-a]pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CC(=O)N=C2SC(C)=C(C)N12 YOQQIZVZVMTRKZ-UHFFFAOYSA-N 0.000 description 1
FOWJATWTQYDPCT-UHFFFAOYSA-N ethyl 2-benzyl-7-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5-carboxylate Chemical compound N=1N2C(C(=O)OCC)=CC(=O)N=C2SC=1CC1=CC=CC=C1 FOWJATWTQYDPCT-UHFFFAOYSA-N 0.000 description 1
XOKOPNAQTOZEPQ-UHFFFAOYSA-N ethyl 3-methyl-7-oxo-2-phenyl-[1,3]thiazolo[3,2-a]pyrimidine-5-carboxylate Chemical compound CC=1N2C(C(=O)OCC)=CC(=O)N=C2SC=1C1=CC=CC=C1 XOKOPNAQTOZEPQ-UHFFFAOYSA-N 0.000 description 1
IMZFEYDQJOBCBU-UHFFFAOYSA-N ethyl 7-oxo-2-phenyl-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5-carboxylate Chemical compound N=1N2C(C(=O)OCC)=CC(=O)N=C2SC=1C1=CC=CC=C1 IMZFEYDQJOBCBU-UHFFFAOYSA-N 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000036039 immunity Effects 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA278,986A 1976-06-04 1977-05-24 Derivatives of thiazolo-[3,2-a]pyrimidin-7-one and thiadiazolo-[3,2-a]pyrimidin-7-one Expired CA1088063A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19762625117 DE2625117A1 (de)	1976-06-04	1976-06-04	Neue heterocyclische verbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
DEP2625117.2		1976-06-04

Publications (1)

Publication Number	Publication Date
CA1088063A true CA1088063A (en)	1980-10-21

Family

ID=5979809

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA278,986A Expired CA1088063A (en)	1976-06-04	1977-05-24	Derivatives of thiazolo-[3,2-a]pyrimidin-7-one and thiadiazolo-[3,2-a]pyrimidin-7-one

Country Status (7)

Country	Link
AT (1)	AT351038B (da)
BE (1)	BE855334A (da)
CA (1)	CA1088063A (da)
DE (1)	DE2625117A1 (da)
DK (1)	DK142175C (da)
SE (1)	SE7706349L (da)
ZA (1)	ZA772502B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2755615A1 (de) *	1977-12-14	1979-06-21	Gruenenthal Gmbh	Neue heterocyclische verbindungen, diese enthaltende arzneimittel und verfahren zu ihrer herstellung

1976
- 1976-06-04 DE DE19762625117 patent/DE2625117A1/de not_active Withdrawn
1977
- 1977-03-30 AT AT221377A patent/AT351038B/de not_active IP Right Cessation
- 1977-04-26 ZA ZA00772502A patent/ZA772502B/xx unknown
- 1977-05-24 CA CA278,986A patent/CA1088063A/en not_active Expired
- 1977-05-31 SE SE7706349A patent/SE7706349L/xx unknown
- 1977-06-02 BE BE178149A patent/BE855334A/xx unknown
- 1977-06-03 DK DK247577A patent/DK142175C/da active

Also Published As

Publication number	Publication date
DK142175B (da)	1980-09-15
ATA221377A (de)	1978-12-15
SE7706349L (sv)	1977-12-05
BE855334A (fr)	1977-10-03
AT351038B (de)	1979-07-10
DK142175C (da)	1981-02-09
DK247577A (da)	1977-12-05
ZA772502B (en)	1978-04-26
DE2625117A1 (de)	1977-12-15

Legal Events

Date	Code	Title	Description
1997-10-21	MKEX	Expiry

Publication	Publication Date	Title
CA1157470A (en)	1983-11-22	Imidazo[1,2,a]pyridine derivatives useful in therapy and their preparations
SU1681728A3 (ru)	1991-09-30	Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты
FI66383C (fi)	1984-10-10	Foerfarande foer framstaellning av farmakologiskt aktiva xantinderivat
ES2284256T3 (es)	2007-11-01	Medicamentos para la diabetes.
EP0357788B1 (en)	1993-11-03	Pyridazinone derivatives
KR920003559B1 (ko)	1992-05-04	만성 당뇨병의 합병증 치료용 피리도-피리다지논 아세트산
US3538086A (en)	1970-11-03	4-oxo-4h-pyrimido 2,1-b benzothiazoles
US4237136A (en)	1980-12-02	Pharmaceutical compositions and methods of using thiadiazolo pyrimidinone compounds
EP0158494B1 (en)	1990-03-07	Penam derivatives and process for preparing the same
CA1088063A (en)	1980-10-21	Derivatives of thiazolo-[3,2-a]pyrimidin-7-one and thiadiazolo-[3,2-a]pyrimidin-7-one
US5116837A (en)	1992-05-26	2,9-dihydro-(6 or 7)-(3-oxo-2,3,4,5-tetrahydropyridazinyl)-pyrazolo [4,3-B]-1,4-benzoxazines
EP0236929B1 (en)	1991-02-06	1,2-dithiol-3-thione derivatives, a process for preparing them and a pharmaceutical composition containing them
NO125675B (da)	1972-10-16
US4432990A (en)	1984-02-21	5-Aminoimidazoles as immunoregulants
CA2049490A1 (en)	1992-03-01	Pyrrolobenzimidazoles, imidazobenzoxazinones and imidazoquinolones, process for their preparation and their use and preparations containing the compounds
JPS60126284A (ja)	1985-07-05	ピリドンカルボン酸誘導体およびその塩
GB2034704A (en)	1980-06-11	2,6-daiminonebularines
US3426017A (en)	1969-02-04	Sulfonylurea compounds
US3506669A (en)	1970-04-14	Derivatives of 2,4-diamino-3-thiophenecarboxylic acid
US4451475A (en)	1984-05-29	Cyclic sulphenamide compounds, their production and their medicinal use
PT545413E (pt)	2000-10-31	Novos analogos de trans-ciclopentanil-purina uteis como imunossupressores
US4745118A (en)	1988-05-17	Substituted quinazoline-3-oxides providing pharmacological activity
US3518256A (en)	1970-06-30	2 - (2 - (5 - nitro - 2 - furyl)vinyl)pyridine derivatives and process for preparation thereof
US4281120A (en)	1981-07-28	7H-1,3,4-Thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic compounds
JPS62240678A (ja)	1987-10-21	複素環で置換されたベンズイミダゾ−ル、その製法及びこれを含有する心臓−及び循環疾病の治療剤