IE50404B1 - Antiallergic and antiulcer 1-oxo-1h-thiazolo(3,2-a)pyrimidine-2-carboxamides and intermediates therefor - Google Patents

Antiallergic and antiulcer 1-oxo-1h-thiazolo(3,2-a)pyrimidine-2-carboxamides and intermediates therefor

Info

Publication number: IE50404B1
Authority: IE; Ireland
Prior art keywords: oxo; compound; hydrogen; carbon atoms; pyrimidine
Prior art date: 1979-11-23

Application number

IE2418/80A

Other languages

English (en)

Other versions

IE802418L (en

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.)

1979-11-23

Filing date

1980-11-21

Publication date

1986-04-16

1980-11-21 Application filed by Pfizer filed Critical Pfizer

1981-05-23 Publication of IE802418L publication Critical patent/IE802418L/xx

1986-04-16 Publication of IE50404B1 publication Critical patent/IE50404B1/en

Links

230000003266 anti-allergic effect Effects 0.000 title claims abstract description 15
230000000767 anti-ulcer Effects 0.000 title claims description 11
239000000543 intermediate Substances 0.000 title abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 62
239000002253 acid Substances 0.000 claims abstract description 45
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
239000001257 hydrogen Substances 0.000 claims abstract description 40
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000002947 alkylene group Chemical group 0.000 claims abstract description 12
150000002431 hydrogen Chemical group 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 59
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
238000010438 heat treatment Methods 0.000 claims description 28
238000000034 method Methods 0.000 claims description 26
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
241001465754 Metazoa Species 0.000 claims description 16
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 14
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 9
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238000010168 coupling process Methods 0.000 claims description 6
238000005859 coupling reaction Methods 0.000 claims description 6
208000007107 Stomach Ulcer Diseases 0.000 claims description 5
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238000011282 treatment Methods 0.000 claims description 5
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AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 3
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ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 description 62
239000000047 product Substances 0.000 description 59
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239000007787 solid Substances 0.000 description 32
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150000001408 amides Chemical class 0.000 description 14
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239000013014 purified material Substances 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
206010041232 sneezing Diseases 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000007711 solidification Methods 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent 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
235000012222 talc Nutrition 0.000 description 1
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 description 1
UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Thiazole And Isothizaole Compounds (AREA)

IE2418/80A 1979-11-23 1980-11-21 Antiallergic and antiulcer 1-oxo-1h-thiazolo(3,2-a)pyrimidine-2-carboxamides and intermediates therefor IE50404B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US9663179A	1979-11-23	1979-11-23

Publications (2)

Publication Number	Publication Date
IE802418L IE802418L (en)	1981-05-23
IE50404B1 true IE50404B1 (en)	1986-04-16

Family

ID=22258306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2418/80A IE50404B1 (en)	1979-11-23	1980-11-21	Antiallergic and antiulcer 1-oxo-1h-thiazolo(3,2-a)pyrimidine-2-carboxamides and intermediates therefor

Country Status (35)

Country	Link
JP (1)	JPS5687586A (fr)
KR (1)	KR830004322A (fr)
AR (2)	AR228859A1 (fr)
AT (1)	AT380883B (fr)
AU (1)	AU520995B2 (fr)
BE (1)	BE886319A (fr)
CA (1)	CA1143731A (fr)
CH (1)	CH649299A5 (fr)
CS (1)	CS241476B2 (fr)
DD (1)	DD154608A5 (fr)
DE (2)	DE3043979C2 (fr)
DK (1)	DK151811C (fr)
EG (1)	EG14929A (fr)
ES (1)	ES8203363A1 (fr)
FI (1)	FI67706C (fr)
FR (1)	FR2470132A1 (fr)
GB (1)	GB2063862B (fr)
GR (1)	GR72132B (fr)
GT (1)	GT198066458A (fr)
HU (1)	HU179091B (fr)
IE (1)	IE50404B1 (fr)
IL (1)	IL61535A (fr)
IN (1)	IN154926B (fr)
IT (1)	IT1209373B (fr)
LU (1)	LU82950A1 (fr)
NL (1)	NL182565C (fr)
NO (1)	NO803521L (fr)
NZ (1)	NZ195596A (fr)
PH (1)	PH16666A (fr)
PL (1)	PL132354B1 (fr)
PT (1)	PT72090B (fr)
SE (1)	SE448732B (fr)
SU (1)	SU1042620A3 (fr)
YU (1)	YU41953B (fr)
ZA (1)	ZA807293B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8300728D0 (en) *	1983-01-12	1983-02-16	Erba Farmitalia	Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives
US4457932A (en) *	1983-07-22	1984-07-03	Bristol-Myers Company	Anti-ulcer agents
GB8422916D0 (en) *	1984-09-11	1984-10-17	May & Baker Ltd	Compositions of matter
JP2690742B2 (ja) *	1987-03-30	1997-12-17	第一製薬株式会社	複素環アミン誘導体
DE68926473T2 (de) *	1988-03-28	1996-10-02	Janssen Pharmaceutica Nv	Mittel zur Konservierung oder Wiederherstellung der gesunden Haut
TWI500623B (zh) *	2009-10-13	2015-09-21	Torrent Pharmaceuticals Ltd	新穎稠合噻唑及噁唑嘧啶酮

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1331059A (en) *	1971-04-19	1973-09-19	Lilly Industries Ltd	Pyrimidotriazinone compounds
US4041163A (en) *	1976-03-29	1977-08-09	Pfizer Inc.	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents
DE2810863A1 (de) *	1978-03-13	1979-09-27	Boehringer Mannheim Gmbh	1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazol-derivate und verfahren zu ihrer herstellung
US4223031A (en) *	1978-05-05	1980-09-16	Mead Johnson & Company	Azolopyrimidinones

1980
- 1980-09-30 DK DK413180A patent/DK151811C/da not_active IP Right Cessation
- 1980-10-15 IN IN760/DEL/80A patent/IN154926B/en unknown
- 1980-11-17 SU SU803212053A patent/SU1042620A3/ru active
- 1980-11-18 AR AR283276A patent/AR228859A1/es active
- 1980-11-18 GB GB8036904A patent/GB2063862B/en not_active Expired
- 1980-11-18 CS CS807820A patent/CS241476B2/cs unknown
- 1980-11-18 HU HU80802755A patent/HU179091B/hu not_active IP Right Cessation
- 1980-11-19 EG EG723/80A patent/EG14929A/xx active
- 1980-11-19 CH CH8567/80A patent/CH649299A5/fr not_active IP Right Cessation
- 1980-11-20 GR GR63413A patent/GR72132B/el unknown
- 1980-11-20 YU YU2950/80A patent/YU41953B/xx unknown
- 1980-11-20 NZ NZ195596A patent/NZ195596A/en unknown
- 1980-11-21 FR FR8024822A patent/FR2470132A1/fr active Granted
- 1980-11-21 IT IT8026176A patent/IT1209373B/it active
- 1980-11-21 NO NO803521A patent/NO803521L/no unknown
- 1980-11-21 ES ES497066A patent/ES8203363A1/es not_active Expired
- 1980-11-21 CA CA000365258A patent/CA1143731A/fr not_active Expired
- 1980-11-21 SE SE8008189A patent/SE448732B/sv not_active IP Right Cessation
- 1980-11-21 IE IE2418/80A patent/IE50404B1/en unknown
- 1980-11-21 FI FI803628A patent/FI67706C/fi not_active IP Right Cessation
- 1980-11-21 NL NLAANVRAGE8006362,A patent/NL182565C/xx not_active IP Right Cessation
- 1980-11-21 DE DE3043979A patent/DE3043979C2/de not_active Expired
- 1980-11-21 IL IL61535A patent/IL61535A/xx unknown
- 1980-11-21 LU LU82950A patent/LU82950A1/fr unknown
- 1980-11-21 JP JP16450280A patent/JPS5687586A/ja active Granted
- 1980-11-21 ZA ZA00807293A patent/ZA807293B/xx unknown
- 1980-11-21 DE DE3050491A patent/DE3050491C2/de not_active Expired
- 1980-11-21 PT PT72090A patent/PT72090B/pt not_active IP Right Cessation
- 1980-11-21 AU AU64595/80A patent/AU520995B2/en not_active Ceased
- 1980-11-21 AT AT0570780A patent/AT380883B/de not_active IP Right Cessation
- 1980-11-21 PH PH24891A patent/PH16666A/en unknown
- 1980-11-21 GT GT198066458A patent/GT198066458A/es unknown
- 1980-11-21 DD DD80225391A patent/DD154608A5/de not_active IP Right Cessation
- 1980-11-22 KR KR1019800004474A patent/KR830004322A/ko not_active Ceased
- 1980-11-22 PL PL1980228008A patent/PL132354B1/pl unknown
- 1980-11-24 BE BE0/202915A patent/BE886319A/fr not_active IP Right Cessation
1982
- 1982-09-13 AR AR290628A patent/AR231296A1/es active

Also Published As

Publication number	Publication date
PT72090A (en)	1980-12-01
FI67706B (fi)	1985-01-31
FR2470132A1 (fr)	1981-05-29
DE3043979A1 (de)	1981-09-03
PL132354B1 (en)	1985-02-28
ZA807293B (en)	1981-12-30
PL228008A1 (fr)	1981-12-11
IL61535A (en)	1984-06-29
CH649299A5 (fr)	1985-05-15
DK413180A (da)	1981-05-24
FI803628L (fi)	1981-05-24
AR231296A1 (es)	1984-10-31
DK151811B (da)	1988-01-04
NL8006362A (nl)	1981-06-16
CS782080A2 (en)	1985-06-13
DD154608A5 (de)	1982-04-07
GT198066458A (es)	1982-05-15
CA1143731A (fr)	1983-03-29
AT380883B (de)	1986-07-25
NO803521L (no)	1981-05-25
GR72132B (fr)	1983-09-19
IN154926B (fr)	1984-12-22
SE448732B (sv)	1987-03-16
KR830004322A (ko)	1983-07-09
SU1042620A3 (ru)	1983-09-15
IT8026176A0 (it)	1980-11-21
HU179091B (en)	1982-08-28
FI67706C (fi)	1985-05-10
YU41953B (en)	1988-02-29
AR228859A1 (es)	1983-04-29
SE8008189L (sv)	1981-05-24
PT72090B (en)	1981-09-29
LU82950A1 (fr)	1981-06-04
ES497066A0 (es)	1982-04-01
IT1209373B (it)	1989-07-16
GB2063862A (en)	1981-06-10
GB2063862B (en)	1983-06-22
IE802418L (en)	1981-05-23
DE3050491C2 (de)	1985-10-10
YU295080A (en)	1983-06-30
NL182565C (nl)	1988-04-05
PH16666A (en)	1983-12-13
CS241476B2 (en)	1986-03-13
ATA570780A (de)	1985-12-15
EG14929A (en)	1989-01-30
IL61535A0 (en)	1980-12-31
JPS617432B2 (fr)	1986-03-06
BE886319A (fr)	1981-05-25
FR2470132B1 (fr)	1983-07-29
AU6459580A (en)	1981-05-28
ES8203363A1 (es)	1982-04-01
DE3043979C2 (de)	1986-08-21
NZ195596A (en)	1984-05-31
AU520995B2 (en)	1982-03-11
NL182565B (nl)	1987-11-02
DK151811C (da)	1988-06-06
JPS5687586A (en)	1981-07-16

Publication	Publication Date	Title
US4233299A (en)	1980-11-11	4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides and salts thereof
US4209623A (en)	1980-06-24	Pyrimidine-5-N-(1H-tetrazol-5-yl)-carboxamides
US4075343A (en)	1978-02-21	Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and derivatives thereof
EP0966454B1 (fr)	2003-05-07	Heterocycles bicycliques disubstitues, production et utilisation comme medicaments
HU188852B (en)	1986-05-28	Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer
US4041163A (en)	1977-08-09	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents
US4734413A (en)	1988-03-29	Substituted 1,2,4-triazolo[1,5-A]triazines as bronchodilators
US4293549A (en)	1981-10-06	Quinolinyl guanidines having antiinflammatory, analgesic or antipyretic activity
US4017625A (en)	1977-04-12	Anti-allergic N-(5-tetrazolyl)-1-oxo-1H-6-alkoxypyrimido-[1,2-a]quinoline-2-carboxamides and intermediates therefor
US4423048A (en)	1983-12-27	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
US4535081A (en)	1985-08-13	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
CA1143731A (fr)	1983-03-29	1-oxo-1h-tetrazolo¬3,2-a\| pyrimidine-2- carboxylate, compose antiallergique et anti-ulceres
US4414388A (en)	1983-11-08	1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
US4321372A (en)	1982-03-23	Antiulcer thiazol-2-ylcarbamoyl-carboxylic acids, esters and amides
US4705787A (en)	1987-11-10	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
CA1060441A (fr)	1979-08-14	Composes antiallergiques de type n-(5-tetrazoly)-1-oxo-1h-6-alkox-ypyrimido (1,2-a)-quinoline-2-carboxamides et composes intermediaires pour leur preparation
JPH01319487A (ja)	1989-12-25	イミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤
EP0121341B1 (fr)	1988-11-17	Triazolo(4,3-c)pyrimidines et triazolo(1,5-c)pyrimidines substituées par des hétérocycles comportant de l'azote
US4085213A (en)	1978-04-18	Tetrazolo[A]quinazol-5-ones antiallergy and antiulcer agents
US4141979A (en)	1979-02-27	Tetrazolo[a]quinazol-5-ones antiallergy and antiulcer agents
FI71158C (fi)	1986-11-24	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-xo-1h-tiazolo/3,2-a/pyrimidin-2-karboxylsyror
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