CA1216238A - Methodes et produits pharmacotherapie - Google Patents

Methodes et produits pharmacotherapie

Info

Publication number: CA1216238A
Authority: CA; Canada
Prior art keywords: alkyl; integer; inclusive; hydrogen; pepstatin
Prior art date: 1982-07-12
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

CA000432021A

Other languages

English (en)

Inventor

Joseph P. Buyniski

Maxwell Gordon

Robert L. Cavanagh

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.)

Bristol Myers Co

Original Assignee

Bristol Myers Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-07-12

Filing date

1983-07-07

Publication date

1987-01-06

1983-07-07 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1987-01-06 Application granted granted Critical

1987-01-06 Publication of CA1216238A publication Critical patent/CA1216238A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 40
238000000034 method Methods 0.000 title description 28
229950000964 pepstatin Drugs 0.000 claims abstract description 82
108010091212 pepstatin Proteins 0.000 claims abstract description 81
FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 claims abstract description 81
238000011282 treatment Methods 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 121
-1 hydroxy, 2,3-dihydroxypropyl Chemical group 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 36
239000012453 solvate Substances 0.000 claims description 30
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 27
231100000252 nontoxic Toxicity 0.000 claims description 27
230000003000 nontoxic effect Effects 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
208000008469 Peptic Ulcer Diseases 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
230000001175 peptic effect Effects 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000002552 dosage form Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
230000000026 anti-ulcerogenic effect Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 claims 6
239000003937 drug carrier Substances 0.000 claims 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
KSBYXRUNSLGUNE-UHFFFAOYSA-N 3-amino-4-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]cyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(N)=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 KSBYXRUNSLGUNE-UHFFFAOYSA-N 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 27
230000000694 effects Effects 0.000 abstract description 22
102000057297 Pepsin A Human genes 0.000 abstract description 17
108090000284 Pepsin A Proteins 0.000 abstract description 17
229940111202 pepsin Drugs 0.000 abstract description 16
229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract description 8
230000000767 anti-ulcer Effects 0.000 abstract description 8
239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 8
230000003247 decreasing effect Effects 0.000 abstract description 4
239000008139 complexing agent Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
230000002496 gastric effect Effects 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
229960001380 cimetidine Drugs 0.000 description 19
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 19
241000700159 Rattus Species 0.000 description 18
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 18
229910001868 water Inorganic materials 0.000 description 18
125000006308 propyl amino group Chemical group 0.000 description 17
238000012360 testing method Methods 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
229960000620 ranitidine Drugs 0.000 description 16
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000007787 solid Substances 0.000 description 14
208000025865 Ulcer Diseases 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
230000036515 potency Effects 0.000 description 10
210000002784 stomach Anatomy 0.000 description 10
231100000397 ulcer Toxicity 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
241000282472 Canis lupus familiaris Species 0.000 description 8
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000003814 drug Substances 0.000 description 8
230000003628 erosive effect Effects 0.000 description 8
238000003756 stirring Methods 0.000 description 8
YSMRPDXIWIIOTG-UHFFFAOYSA-N 4-[3-(piperidin-1-ylmethyl)phenoxy]butan-1-amine Chemical compound NCCCCOC1=CC=CC(CN2CCCCC2)=C1 YSMRPDXIWIIOTG-UHFFFAOYSA-N 0.000 description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000000523 sample Substances 0.000 description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
239000003921 oil Substances 0.000 description 6
230000028327 secretion Effects 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
231100000673 dose–response relationship Toxicity 0.000 description 5
238000010828 elution Methods 0.000 description 5
210000004211 gastric acid Anatomy 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
241001024304 Mino Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000010171 animal model Methods 0.000 description 4
230000001262 anti-secretory effect Effects 0.000 description 4
208000000718 duodenal ulcer Diseases 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000035876 healing Effects 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
206010017865 Gastritis erosive Diseases 0.000 description 3
229910017974 NH40H Inorganic materials 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
208000007107 Stomach Ulcer Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
238000003304 gavage Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
230000036269 ulceration Effects 0.000 description 3
DRLLEHPFGRESBT-UHFFFAOYSA-N 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate;hydron;dichloride Chemical compound Cl.Cl.C1CN(CCOC(=O)C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 DRLLEHPFGRESBT-UHFFFAOYSA-N 0.000 description 2
SZBNZTGCAMLMJY-UHFFFAOYSA-N 3,4-dimethoxycyclobut-3-ene-1,2-dione Chemical compound COC1=C(OC)C(=O)C1=O SZBNZTGCAMLMJY-UHFFFAOYSA-N 0.000 description 2
VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
206010065713 Gastric Fistula Diseases 0.000 description 2
102000003710 Histamine H2 Receptors Human genes 0.000 description 2
108090000050 Histamine H2 Receptors Proteins 0.000 description 2
241000243251 Hydra Species 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
DHUZAAUGHUHIDS-ONEGZZNKSA-N Isomyristicin Chemical compound COC1=CC(\C=C\C)=CC2=C1OCO2 DHUZAAUGHUHIDS-ONEGZZNKSA-N 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003699 antiulcer agent Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229960000530 carbenoxolone Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 2
201000006549 dyspepsia Diseases 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
235000011389 fruit/vegetable juice Nutrition 0.000 description 2
201000005917 gastric ulcer Diseases 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
229960005439 propantheline bromide Drugs 0.000 description 2
210000001187 pylorus Anatomy 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
235000002020 sage Nutrition 0.000 description 2
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125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
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NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
YWUNVHXKGMPHDM-AMTQNMNTSA-N (2s)-2-[[(2e,4e,6e,11r)-12-[(4s,4as,6r,8s,8ar)-4-[[(2s)-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetyl]amino]-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4h-pyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4,6-trienoyl]amino Chemical compound CO[C@]1([C@H](O)C(=O)N[C@H]2OCO[C@@H]3[C@H](C([C@@H](C[C@H](O)CCC\C=C\C=C\C=C\C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)O[C@@H]32)(C)C)OC)CC(=C)[C@@H](C)[C@@H](C)O1 YWUNVHXKGMPHDM-AMTQNMNTSA-N 0.000 description 1
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WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
CHZXTOCAICMPQR-UHFFFAOYSA-N 2-(2-bromoethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCBr)C(=O)C2=C1 CHZXTOCAICMPQR-UHFFFAOYSA-N 0.000 description 1
VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
125000006321 2-propynyl amino group Chemical group [H]C#CC([H])([H])N([H])* 0.000 description 1
KZHFWNYETNRKCY-UHFFFAOYSA-N 3-[3-(3,6-dihydro-2h-pyridin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CC=CCC2)=C1 KZHFWNYETNRKCY-UHFFFAOYSA-N 0.000 description 1
DXFZTDREQLPNEI-UHFFFAOYSA-N 3-[3-(azepan-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCCC2)=C1 DXFZTDREQLPNEI-UHFFFAOYSA-N 0.000 description 1
QUHOGPYKODZMKL-UHFFFAOYSA-N 3-[3-[(4-methylpiperazin-1-yl)methyl]phenoxy]propan-1-amine Chemical compound C1CN(C)CCN1CC1=CC=CC(OCCCN)=C1 QUHOGPYKODZMKL-UHFFFAOYSA-N 0.000 description 1
WEKYWIBCHONDBC-UHFFFAOYSA-N 3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=N1 WEKYWIBCHONDBC-UHFFFAOYSA-N 0.000 description 1
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AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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210000002417 xiphoid bone Anatomy 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA000432021A 1982-07-12 1983-07-07 Methodes et produits pharmacotherapie Expired CA1216238A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US39727782A	1982-07-12	1982-07-12
US397,277		1982-07-12
DK010784A DK165546C (da)	1982-07-12	1984-01-10	Farmaceutisk praeparat til behandling af peptisk ulcus paa enhedsdosisform

Publications (1)

Publication Number	Publication Date
CA1216238A true CA1216238A (fr)	1987-01-06

Family

ID=26063319

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000432021A Expired CA1216238A (fr)	1982-07-12	1983-07-07	Methodes et produits pharmacotherapie

Country Status (2)

Country	Link
CA (1)	CA1216238A (fr)
DK (2)	DK318783D0 (fr)

1983
- 1983-07-07 CA CA000432021A patent/CA1216238A/fr not_active Expired
- 1983-07-11 DK DK3187/83A patent/DK318783D0/da not_active Application Discontinuation
1984
- 1984-01-10 DK DK010784A patent/DK165546C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK10784D0 (da)	1984-01-10
DK165546B (da)	1992-12-14
DK318783D0 (da)	1983-07-11
DK165546C (da)	1993-05-03
DK10784A (da)	1985-07-11

Legal Events

Date	Code	Title	Description
2004-01-06	MKEX	Expiry

Publication	Publication Date	Title
CA1190224A (fr)	1985-07-09	Derives de la 1,2-diamino-cyclobutene-3,4-dione puissant antagoniste de l'histamine h.sub.2
SU1400508A3 (ru)	1988-05-30	Способ получени производных арилтиазолов
DE2623567C2 (de)	1984-03-01	Thienopyridinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittelzubereitungen
IE44124B1 (en)	1981-08-26	Cyclobutene-diones
JPS6229566A (ja)	1987-02-07	新規グアニジノメチル安息香酸誘導体
EP0508220A1 (fr)	1992-10-14	Dérivées d'amidino-phenylalanine, procédé de leur préparation, leur utilisation et composition les contenants
DE2938302A1 (de)	1980-04-03	Neue derivate des 3-(aminoaethyl)- phenols und deren salze, deren herstellungsverfahren, deren verwendung als arzneimittel und die diese enthaltenden pharmazeutischen zusammensetzungen
DE3209708A1 (de)	1982-10-21	Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
EP0099122B1 (fr)	1986-10-22	Compositions à base de pepstatine et d'un antagoniste des récepteurs d'histamine H2 ayant une activité anti-ulcére augmentée
US4522943A (en)	1985-06-11	Chemical compounds
NO783053L (no)	1979-03-09	Fremgangsmaate for fremstilling av farmakologisk aktive amidinozulfonsyrederivater
EP0093252B1 (fr)	1988-03-09	Dérivés de thiométhylpyridine, procédé pour leur préparation et médicaments les contenant
CA1216238A (fr)	1987-01-06	Methodes et produits pharmacotherapie
DE3875820T2 (de)	1993-03-18	Aromatische heterozyklische karbonsaeureamidabkoemmlinge, verfahren zur herstellung und arzneimittel, die diese enthalten.
PT85555B (pt)	1990-05-31	Processo para a preparacao de quinazolinodionas e piridopirimidinodionas
NO883263L (no)	1989-01-24	Fremgangsmaate for fremstilling av terapeutisk aktive benzimidazol-derivater.
DE3685942T2 (de)	1992-12-24	2-pyridylessigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen.
US4386211A (en)	1983-05-31	Anti-ulcer urea compounds
US4539316A (en)	1985-09-03	Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones
DE2734270C2 (fr)	1990-06-21
SU791241A3 (ru)	1980-12-23	Способ получени производных 4,5,6,7-тетрагидроимидазо 4,5-с пиридина
SK695188A3 (en)	1996-02-07	Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent
NO152214B (no)	1985-05-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-cyano-n`-(2-((4-metyl-5-imidazolyl)-metyltio)etyl-n"-alknylguanidiner
DE3880348T2 (de)	1993-11-04	N-substituierte alpha-mercaptomethylbenzenpropanamid-derivate, ihre herstellung, ihre verwendung als arzneimittel und diese enthaltende zusammensetzungen.
JP2851117B2 (ja)	1999-01-27	インドール誘導体およびそれらを有効成分とする抗潰瘍薬