NO772669L - Fremgangsm}te for fremstilling av farmakologisk aktive forbindelser - Google Patents

Fremgangsm}te for fremstilling av farmakologisk aktive forbindelser

Info

Publication number: NO772669L
Authority: NO; Norway
Prior art keywords: formula; het; compound; ring; stated
Prior art date: 1976-07-28

Application number

NO772669A

Other languages

English (en)

Norwegian (no)

Inventor

Graham John Durant

Charon Robin Ganellin

Original Assignee

Smith Kline French Lab

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.)

1976-07-28

Filing date

1977-07-27

Publication date

1978-01-31

1977-07-27 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1978-01-31 Publication of NO772669L publication Critical patent/NO772669L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 46
238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 11
230000000144 pharmacologic effect Effects 0.000 title 1
-1 2-thiazolyl ring Chemical group 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
239000005864 Sulphur Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 2
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
239000000047 product Substances 0.000 claims 3
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 42
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 26
229960001340 histamine Drugs 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
FPKQNDZQVDBFLK-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)propan-1-amine Chemical compound NCCCC1=NC=CS1 FPKQNDZQVDBFLK-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 4
102000003710 Histamine H2 Receptors Human genes 0.000 description 4
108090000050 Histamine H2 Receptors Proteins 0.000 description 4
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125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
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230000001404 mediated effect Effects 0.000 description 3
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
229960000582 mepyramine Drugs 0.000 description 3
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239000000825 pharmaceutical preparation Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 2
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241000700199 Cavia porcellus Species 0.000 description 2
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
229960000520 diphenhydramine Drugs 0.000 description 1
QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
OJHSNWXCKUSASO-UHFFFAOYSA-N methyl N-cyano-N-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound C(#N)N(C(SC)=N)CCSCC1=C(N=CN1)C OJHSNWXCKUSASO-UHFFFAOYSA-N 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000001151 other effect Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 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
230000001225 therapeutic effect Effects 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms

Landscapes

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

NO772669A 1976-07-28 1977-07-27 Fremgangsm}te for fremstilling av farmakologisk aktive forbindelser NO772669L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3139376		1976-07-28

Publications (1)

Publication Number	Publication Date
NO772669L true NO772669L (no)	1978-01-31

Family

ID=10322438

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO772669A NO772669L (no)	1976-07-28	1977-07-27	Fremgangsm}te for fremstilling av farmakologisk aktive forbindelser

Country Status (14)

Country	Link
JP (1)	JPS5315371A (es)
AU (1)	AU2734777A (es)
BE (1)	BE857219R (es)
DE (1)	DE2733952A1 (es)
DK (1)	DK331977A (es)
ES (1)	ES461101A2 (es)
FI (1)	FI772294A7 (es)
FR (1)	FR2359841A1 (es)
IL (1)	IL52545A0 (es)
LU (1)	LU77865A1 (es)
NL (1)	NL7708379A (es)
NO (1)	NO772669L (es)
PL (1)	PL199909A1 (es)
ZA (1)	ZA774221B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4309435A (en)	1978-10-16	1982-01-05	Imperial Chemical Industries Ltd.	Antisecretory guanidine derivatives and pharmaceutical compositions containing them
FR2446829A1 (fr)	1978-11-16	1980-08-14	Glaxo Group Ltd	Derives de polymethylene disubstitues en alpha, omega, procede pour leur preparation et compositions pharmaceutiques les contenant
JPS57102852A (en) *	1980-12-19	1982-06-26	Shionogi & Co Ltd	Dicarboxylic acid diamide
US5352831A (en) *	1987-09-02	1994-10-04	Ciba-Geigy Corporation	Oligomeric cyanoguanidines
ATE70261T1 (de) *	1987-09-02	1991-12-15	Ciba Geigy Ag	Oligomere cyanoguanidine.
EP4196793A1 (en)	2020-08-11	2023-06-21	Université de Strasbourg	H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR735087A (fr) *	1930-09-01	1932-11-03	Anticoman Ges M B H	Procédé pour fabriquer des sels de polyméthylène-biguanidine se dissolvant facilement dans l'eau et dans le suc gastrique
GB1493931A (en) *	1974-02-07	1977-11-30	Smith Kline French Lab	Guanidines isothioureas and thioureas

1977
- 1977-07-14 ZA ZA00774221A patent/ZA774221B/xx unknown
- 1977-07-18 IL IL52545A patent/IL52545A0/xx unknown
- 1977-07-22 DK DK331977A patent/DK331977A/da not_active Application Discontinuation
- 1977-07-26 AU AU27347/77A patent/AU2734777A/en active Pending
- 1977-07-27 BE BE179688A patent/BE857219R/xx active
- 1977-07-27 FR FR7723081A patent/FR2359841A1/fr active Pending
- 1977-07-27 NO NO772669A patent/NO772669L/no unknown
- 1977-07-27 FI FI772294A patent/FI772294A7/fi not_active Application Discontinuation
- 1977-07-27 DE DE19772733952 patent/DE2733952A1/de not_active Withdrawn
- 1977-07-28 LU LU77865A patent/LU77865A1/xx unknown
- 1977-07-28 JP JP9132577A patent/JPS5315371A/ja active Pending
- 1977-07-28 ES ES461101A patent/ES461101A2/es not_active Expired
- 1977-07-28 NL NL7708379A patent/NL7708379A/xx not_active Application Discontinuation
- 1977-07-28 PL PL19990977A patent/PL199909A1/xx unknown

Also Published As

Publication number	Publication date
IL52545A0 (en)	1977-10-31
JPS5315371A (en)	1978-02-13
FR2359841A1 (fr)	1978-02-24
LU77865A1 (es)	1977-10-24
NL7708379A (nl)	1978-01-31
FI772294A7 (es)	1978-01-29
ES461101A2 (es)	1978-12-01
DE2733952A1 (de)	1978-02-02
DK331977A (da)	1978-01-29
BE857219R (fr)	1978-01-27
AU2734777A (en)	1979-02-01
PL199909A1 (pl)	1978-11-20
ZA774221B (en)	1978-06-28

Publication	Publication Date	Title
US3881015A (en)	1975-04-29	Pharmaceutical compositions and methods of inhibiting histamine activity with isothiourea compounds
US3876647A (en)	1975-04-08	Certain n-cyanoguanidines
US4034101A (en)	1977-07-05	N-Oxy and N-amino guanidines
SE416049B (sv)	1980-11-24	Forfarande for framstellning av 1,1-diaminoctylenderivat, som kan anvendas for hemning av vissa histaminverkningar
IE44124B1 (en)	1981-08-26	Cyclobutene-diones
CS199255B2 (en)	1980-07-31	Method of preparing pharmacologically active compounds
CA1062263A (en)	1979-09-11	Histamine h-2 receptor antagonists
US4265896A (en)	1981-05-05	Amidinosulphonic acid derivatives
US4013659A (en)	1977-03-22	Certain n,n'-disubstituted guanidine compounds and their use
US3920822A (en)	1975-11-18	Inhibition of histamine activity with cyanoguanidines
US4070472A (en)	1978-01-24	Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine
NO794346L (no)	1975-09-15	Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser
US4118496A (en)	1978-10-03	Heterocyclic-methylthioalkyl-amidines
US4285952A (en)	1981-08-25	Pyridyl, thiazolyl and isothiazolyl alkyl bisamidines
CS196352B2 (en)	1980-03-31	Process for preparing derivatives of amidinformic acid
US4139624A (en)	1979-02-13	Alkoxypyridyl substituted alkanes
GB1565205A (en)	1980-04-16	Heterocyclic sulphoxides
NO772668L (no)	1978-01-31	Analogifremgangsm}te for fremstilling av farmakologisk aktive forbindelser
US4137319A (en)	1979-01-30	Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine
IE46928B1 (en)	1983-11-02	-halomethyl derivatives of amino acids
US4093729A (en)	1978-06-06	N-Oxy and N-amino guanidines
US4018928A (en)	1977-04-19	Pyridyl substituted aminoalkyl-thioureas and ureas
US4219553A (en)	1980-08-26	Alkoxy pyridyl substituted alkanes
US4151289A (en)	1979-04-24	Nitromethylene amidino derivatives containing imidazole groups
US4210652A (en)	1980-07-01	Pharmacologically active 1,3-bis[1-(2-heteroalkylthio)ethylamino)-2-nitrovinyl-1-amino]propane derivatives