DD202293A5 - Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen - Google Patents

Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen Download PDF

Info

Publication number: DD202293A5
Authority: DD; German Democratic Republic
Prior art keywords: guanidino; formula; mmol; thiazole; compounds
Prior art date: 1980-10-14

Application number

DD81234080A

Other languages

German (de)

English (en)

Inventor

John L Lamattina

Christopher A Lipinski

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.)

1980-10-14

Filing date

1981-10-14

Publication date

1983-09-07

1981-10-14 Application filed by Pfizer filed Critical Pfizer

1983-09-07 Publication of DD202293A5 publication Critical patent/DD202293A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 98
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052794 bromium Inorganic materials 0.000 claims abstract description 16
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 11
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229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
229910052727 yttrium Inorganic materials 0.000 claims abstract description 4
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 2
229910052731 fluorine Inorganic materials 0.000 claims abstract 2
239000011737 fluorine Substances 0.000 claims abstract 2
-1 aralkyl halide Chemical class 0.000 claims description 35
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238000010438 heat treatment Methods 0.000 claims description 5
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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 1
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238000006243 chemical reaction Methods 0.000 description 10
OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 10
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239000002198 insoluble material Substances 0.000 description 9
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FQOXJJNWHXRGIV-UHFFFAOYSA-N 2-[4-(2-aminoacetyl)-1,3-thiazol-2-yl]guanidine;dihydrochloride Chemical compound Cl.Cl.NCC(=O)C1=CSC(NC(N)=N)=N1 FQOXJJNWHXRGIV-UHFFFAOYSA-N 0.000 description 7
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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 6
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MZJZNADJWQEIIG-UHFFFAOYSA-N 1-(2-methyl-1h-imidazol-5-yl)ethanone Chemical compound CC(=O)C1=CN=C(C)N1 MZJZNADJWQEIIG-UHFFFAOYSA-N 0.000 description 5
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
MCLITRXWHZUNCQ-UHFFFAOYSA-N methylcyanamide Chemical compound CNC#N MCLITRXWHZUNCQ-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
RYYCFQTWLMFJIG-UHFFFAOYSA-N propylcyanamide Chemical compound CCCNC#N RYYCFQTWLMFJIG-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012066 reaction slurry Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000028327 secretion Effects 0.000 description 1
150000004760 silicates Chemical class 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
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 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
229940095064 tartrate Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005556 thienylene group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD81234080A 1980-10-14 1981-10-14 Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen DD202293A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US19623180A	1980-10-14	1980-10-14
US06/293,574 US4374843A (en)	1980-10-14	1981-08-20	2-Guanidino-4-heteroarylthiazoles

Publications (1)

Publication Number	Publication Date
DD202293A5 true DD202293A5 (de)	1983-09-07

Family

ID=26891753

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
DD81234080A DD202293A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DD81248821A DD207719A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DD81248822A DD207913A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DD81248820A DD207718A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
DD81248821A DD207719A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DD81248822A DD207913A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DD81248820A DD207718A5 (de)	1980-10-14	1981-10-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen

Country Status (28)

Country	Link
US (1)	US4374843A (pl)
EP (1)	EP0050458B1 (pl)
KR (1)	KR850001858B1 (pl)
AR (3)	AR228675A1 (pl)
AT (1)	ATE11048T1 (pl)
AU (2)	AU530589B2 (pl)
CA (1)	CA1156239A (pl)
CS (1)	CS231182B2 (pl)
DD (4)	DD202293A5 (pl)
DE (1)	DE3168067D1 (pl)
DK (1)	DK453181A (pl)
ES (4)	ES8301978A1 (pl)
FI (1)	FI75821C (pl)
GR (1)	GR75098B (pl)
HK (1)	HK52387A (pl)
HU (2)	HU191895B (pl)
IE (1)	IE51642B1 (pl)
IL (1)	IL64035A (pl)
KE (1)	KE3707A (pl)
MY (1)	MY8700512A (pl)
NO (1)	NO159654C (pl)
NZ (1)	NZ198629A (pl)
PH (3)	PH17562A (pl)
PL (3)	PL135331B1 (pl)
PT (1)	PT73817B (pl)
SG (1)	SG23487G (pl)
SU (1)	SU1153829A3 (pl)
YU (4)	YU42434B (pl)

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US4482723A (en) *	1983-04-11	1984-11-13	Pfizer Inc.	Process for preparation of 4-acetyl-2-substituted-imidazoles
US4435396A (en) *	1982-05-10	1984-03-06	Pfizer Inc.	Antiulcer 2-guanidino-4-(2-substituted-amino-4-imidazolyl)thiazoles and process therefor
AU542287B2 (en) *	1982-06-17	1985-02-14	Toyama Chemical Co. Ltd.	Process for producing 2-(2-aminothiazol-4-yl) glyoxylic acid derivative, it:s salt and intermediates therefor
EP0156644A1 (en) *	1984-04-02	1985-10-02	Pfizer Inc.	Process and intermediates for 4-acetylimidazoles
US4560690A (en) *	1984-04-30	1985-12-24	Pfizer Inc.	2-(N-substituted guanidino)-4-hetero-arylthiazole antiulcer agents
US4567179A (en) *	1984-10-11	1986-01-28	Pfizer, Inc.	Antiinflammatory salts of piroxicam
US4632993A (en) *	1984-10-11	1986-12-30	Pfizer Inc.	Process for making 2-guanidino-4-(2-methyl-4-imidazolyl) thiazole dihydrobromide
US4591595A (en) *	1984-10-11	1986-05-27	Pfizer Inc.	2-guanidino-4-(2-methyl-4-imidazolyl)thiazoles in the treatment of rheumatoid arthritis
WO1986003203A1 (fr) *	1984-11-22	1986-06-05	Yoshitomi Pharmaceutical Industries, Ltd.	Derives de thienylthiazole
US4814341A (en) *	1986-08-26	1989-03-21	Reiter Lawrence A	2-guanidino-4-(2-furyl) thiazoles as antiulcer agents
EP0259085B1 (en) *	1986-08-29	1991-08-21	Pfizer Inc.	2-guanidino-4-arylthiazoles for treatment of peptic ulcers
ATE106884T1 (de) *	1986-10-29	1994-06-15	Pfizer	Verfahren zur herstellung von 2-(1-pentyl-3- guanidino)-4-(2-methyl-4-imidazolyl)thiazol und dessen kristallinisches dihydrochlorid-trihydrat.
IL95548A0 (en) *	1989-09-15	1991-06-30	Fujisawa Pharmaceutical Co	Thiazole derivatives,processes for the preparation thereof and pharmaceutical composition containing the same
WO1992016526A1 (en) *	1991-03-13	1992-10-01	Fujisawa Pharmaceutical Co., Ltd.	Thiazole derivatives
SI0928793T1 (en) *	1998-01-02	2002-10-31	F. Hoffmann-La Roche Ag	Thiazole derivatives
CN101287711A (zh) *	2005-08-23	2008-10-15	宇部兴产株式会社	1-取代-5-酰基咪唑化合物的制备方法
US9499533B2 (en)	2012-03-27	2016-11-22	Shionogi & Co., Ltd.	Aromatic 5-membered heterocyclic derivative having TRPV4-Inhibiting activity
KR20220119653A (ko)	2019-12-20	2022-08-30	테나야 테라퓨틱스, 인코포레이티드	플루오로알킬-옥사디아졸 및 이의 용도
WO2022034121A1 (en)	2020-08-11	2022-02-17	Université De Strasbourg	H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

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FR1516777A (fr) *	1966-08-02	1968-02-05	Innothera Lab Sa	Dérivés du thiazole ainsi que de la thiazolo [4,5-d] pyridazine et leur préparation
US3519637A (en) *	1966-12-06	1970-07-07	Hoffmann La Roche	1-(4-thiazolylmethyl)nitroimidazole derivatives
BE758146A (fr) *	1969-10-29	1971-04-28	Smith Kline French Lab	Derives de l'amidine
US3950353A (en) *	1971-03-09	1976-04-13	Smith Kline & French Laboratories Limited	Pharmacologically active thiourea and urea compounds
HU168776B (pl) *	1973-11-09	1976-07-28
DE2614189A1 (de) *	1976-04-02	1977-10-20	Hoechst Ag	Therapeutisch wirksame ureido- und semicarbazido-derivate des tiazols und verfahren zu ihrer herstellung
NZ186965A (en) *	1977-04-20	1980-02-21	Ici Ltd	Guanidino derivatives and pharmaceutical compositions
JPS54132566A (en) *	1978-01-18	1979-10-15	Ici Ltd	Guanidine derivative*its manufacture and secretion controlling pharmaceutical composition containing it
EP0014057B1 (en) *	1979-01-18	1985-01-02	Imperial Chemical Industries Plc	Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them
US4220654A (en) *	1979-06-04	1980-09-02	Merck & Co., Inc.	Cyclic imidazole cyanoguanidines
AU518569B2 (en) *	1979-08-07	1981-10-08	Farmos-Yhtyma Oy	4-benzyl- and 4-benzoyl imidazole derivatives

1981
- 1981-08-20 US US06/293,574 patent/US4374843A/en not_active Expired - Fee Related
- 1981-10-12 IL IL64035A patent/IL64035A/xx unknown
- 1981-10-12 AT AT81304724T patent/ATE11048T1/de not_active IP Right Cessation
- 1981-10-12 DE DE8181304724T patent/DE3168067D1/de not_active Expired
- 1981-10-12 EP EP81304724A patent/EP0050458B1/en not_active Expired
- 1981-10-12 IE IE2384/81A patent/IE51642B1/en unknown
- 1981-10-13 CS CS817500A patent/CS231182B2/cs unknown
- 1981-10-13 CA CA000387744A patent/CA1156239A/en not_active Expired
- 1981-10-13 FI FI813177A patent/FI75821C/fi not_active IP Right Cessation
- 1981-10-13 KR KR1019810003857A patent/KR850001858B1/ko not_active Expired
- 1981-10-13 SU SU813344744A patent/SU1153829A3/ru active
- 1981-10-13 HU HU833918A patent/HU191895B/hu not_active IP Right Cessation
- 1981-10-13 PH PH26341A patent/PH17562A/en unknown
- 1981-10-13 ES ES506216A patent/ES8301978A1/es not_active Expired
- 1981-10-13 DK DK453181A patent/DK453181A/da not_active Application Discontinuation
- 1981-10-13 NO NO813442A patent/NO159654C/no unknown
- 1981-10-13 NZ NZ198629A patent/NZ198629A/en unknown
- 1981-10-13 YU YU2464/81A patent/YU42434B/xx unknown
- 1981-10-13 HU HU812951A patent/HU186788B/hu not_active IP Right Cessation
- 1981-10-13 GR GR66268A patent/GR75098B/el unknown
- 1981-10-13 AU AU76287/81A patent/AU530589B2/en not_active Ceased
- 1981-10-14 DD DD81234080A patent/DD202293A5/de not_active IP Right Cessation
- 1981-10-14 PT PT73817A patent/PT73817B/pt unknown
- 1981-10-14 PL PL1981241644A patent/PL135331B1/pl unknown
- 1981-10-14 PL PL1981233430A patent/PL134491B1/pl unknown
- 1981-10-14 PL PL1981241643A patent/PL133712B1/pl unknown
- 1981-10-14 DD DD81248821A patent/DD207719A5/de not_active IP Right Cessation
- 1981-10-14 DD DD81248822A patent/DD207913A5/de not_active IP Right Cessation
- 1981-10-14 DD DD81248820A patent/DD207718A5/de not_active IP Right Cessation
1982
- 1982-08-20 ES ES515157A patent/ES515157A0/es active Granted
- 1982-08-20 ES ES515159A patent/ES515159A0/es active Granted
- 1982-08-20 ES ES515158A patent/ES515158A0/es active Granted
- 1982-08-27 AR AR290463A patent/AR228675A1/es active
- 1982-08-27 AR AR290461A patent/AR229703A1/es active
- 1982-08-27 AR AR290462A patent/AR228674A1/es active
1983
- 1983-04-06 PH PH28740A patent/PH18467A/en unknown
- 1983-04-06 PH PH28741A patent/PH17856A/en unknown
- 1983-05-12 YU YU1051/83A patent/YU42076B/xx unknown
- 1983-05-12 YU YU1053/83A patent/YU42078B/xx unknown
- 1983-05-12 YU YU1052/83A patent/YU42077B/xx unknown
1984
- 1984-08-17 AU AU32062/84A patent/AU548992B2/en not_active Ceased
1987
- 1987-03-09 SG SG234/87A patent/SG23487G/en unknown
- 1987-03-20 KE KE3707A patent/KE3707A/xx unknown
- 1987-07-09 HK HK523/87A patent/HK52387A/xx unknown
- 1987-12-30 MY MY512/87A patent/MY8700512A/xx unknown

Also Published As

Publication number	Publication date
DD207718A5 (de)	1984-03-14
ES506216A0 (es)	1982-12-16
DK453181A (da)	1982-04-15
ES8306750A1 (es)	1983-06-01
US4374843A (en)	1983-02-22
YU42434B (en)	1988-08-31
PH17856A (en)	1985-01-09
ES8306751A1 (es)	1983-06-01
IL64035A (en)	1986-01-31
YU105383A (en)	1983-10-31
IE812384L (en)	1982-04-14
YU105183A (en)	1983-10-31
AR228675A1 (es)	1983-03-30
CS750081A2 (en)	1984-02-13
FI813177L (fi)	1982-04-15
KR850001858B1 (ko)	1985-12-28
DE3168067D1 (en)	1985-02-14
PL133712B1 (en)	1985-06-29
DD207719A5 (de)	1984-03-14
PL241643A1 (en)	1983-11-21
NO813442L (no)	1982-04-15
HK52387A (en)	1987-07-17
SU1153829A3 (ru)	1985-04-30
PH17562A (en)	1984-10-01
AU530589B2 (en)	1983-07-21
CA1156239A (en)	1983-11-01
AR228674A1 (es)	1983-03-30
AR229703A1 (es)	1983-10-31
ES8301978A1 (es)	1982-12-16
PL233430A1 (en)	1983-11-21
ES8306749A1 (es)	1983-06-01
CS231182B2 (en)	1984-10-15
GR75098B (pl)	1984-07-13
SG23487G (en)	1987-07-10
AU7628781A (en)	1982-04-22
YU42078B (en)	1988-04-30
ATE11048T1 (de)	1985-01-15
NZ198629A (en)	1985-02-28
NO159654C (no)	1989-01-25
PT73817B (en)	1983-11-07
PL241644A1 (en)	1983-11-21
FI75821B (fi)	1988-04-29
YU105283A (en)	1983-10-31
MY8700512A (en)	1987-12-31
YU246481A (en)	1983-10-31
AU548992B2 (en)	1986-01-09
HU186788B (en)	1985-09-30
ES515157A0 (es)	1983-06-01
IE51642B1 (en)	1987-01-21
DD207913A5 (de)	1984-03-21
PL134491B1 (en)	1985-08-31
NO159654B (no)	1988-10-17
IL64035A0 (en)	1982-01-31
EP0050458B1 (en)	1985-01-02
ES515158A0 (es)	1983-06-01
FI75821C (fi)	1988-08-08
KR830007638A (ko)	1983-11-04
ES515159A0 (es)	1983-06-01
YU42076B (en)	1988-04-30
YU42077B (en)	1988-04-30
EP0050458A2 (en)	1982-04-28
EP0050458A3 (en)	1982-09-01
PT73817A (en)	1981-11-01
PH18467A (en)	1985-07-18
KE3707A (en)	1987-04-03
AU3206284A (en)	1984-11-29
PL135331B1 (en)	1985-10-31
HU191895B (en)	1987-04-28

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3218584C2 (pl)	1989-11-02
DD261787A5 (de)	1988-11-09	Antiarrhythmisch wirksame phenylpiperazin-mittel
DD233374A5 (de)	1986-02-26	Verfahren zur herstellung von 2-(n-subst.-guanidino)-4-heteroarylthiazole
DE69108913T2 (de)	1995-08-24	4-alkylimidazolderivate.
DE2322880C2 (de)	1982-09-23	4-(Imidazolin-2-ylamino)-2,1,3-benzothiadiazole und Verfahren zu deren Herstellung
CH652395A5 (de)	1985-11-15	2(1h)-pyridinon-derivate, ihre herstellung und sie enthaltende pharmazeutische zubereitungen.
DD216929A5 (de)	1985-01-02	Verfahren zur herstellung von thiazolidinderivaten
DD207719A5 (de)	1984-03-14	Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen
DE2928842A1 (de)	1980-02-14	Pyrimidonderivate
DE2847792C2 (pl)	1988-02-04
CH674206A5 (pl)	1990-05-15
DD265403A5 (de)	1989-03-01	Verfahren zum herstellen herzstimulierender chinolene
DE2921660A1 (de)	1980-01-10	5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel
DD209828A5 (de)	1984-05-23	Verfahren zur herstellung von 2-guanidino-4-(2-subst.-amino-4-imidazolyl)thiazolen
DE3728491A1 (de)	1989-03-09	Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DD144916A5 (de)	1980-11-12	Verfahren zur herstellung von pyrimidinverbindungen und ihren salzen
DE3618724C2 (de)	1994-06-16	N-[3-(Nitro)-chinol-4-yl]-carboxamidinamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2832309C2 (pl)	1989-07-06
DE2550959C3 (de)	1980-12-04	Tetrazolyl-imidazole und Tetrazolyl--benzimidazole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE3336409A1 (de)	1985-04-18	Chinazolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2457309A1 (de)	1975-06-05	2-phenylhydrazinothiazolin- beziehungsweise 2-phenylhydrazinothiazininderivate sowie ihre verwendung und verfahren zur herstellung derselben
DE3044566A1 (de)	1982-07-15	N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung
AT375656B (de)	1984-08-27	Verfahren zur herstellung von neuen 3-amino-5(4-pyridyl)-1,2,4-triazol-basen und ihren salzen
JPS6157307B2 (pl)	1986-12-06
DE3413875A1 (de)	1985-10-17	Benzothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltendes arzneimittel