CH618697A5 - - Google Patents

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Info

Publication number: CH618697A5
Authority: CH; Switzerland
Prior art keywords: compound; methoxy; methyl; piperazine; benzoyl
Prior art date: 1974-08-12

Application number

CH1009075A

Other languages

English (en)

Italian (it)

Inventor

Francesco Makovec

Paolo Senin

Luigi Rovati

Original Assignee

Rotta Research 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.)

1974-08-12

Filing date

1975-08-01

Publication date

1980-08-15

1975-08-01 Application filed by Rotta Research Lab filed Critical Rotta Research Lab

1980-08-15 Publication of CH618697A5 publication Critical patent/CH618697A5/it

Links

150000001875 compounds Chemical class 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 19
230000003110 anti-inflammatory effect Effects 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
230000003356 anti-rheumatic effect Effects 0.000 claims description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
235000009518 sodium iodide Nutrition 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
NGQQUXXTDZADNX-UHFFFAOYSA-N 2,3,4,5-tetrachlorofuran Chemical compound ClC=1OC(Cl)=C(Cl)C=1Cl NGQQUXXTDZADNX-UHFFFAOYSA-N 0.000 claims description 2
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims description 2
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims description 2
TXWGINUZLBAKDF-UHFFFAOYSA-N N-Deschlorobenzoyl indomethacin Chemical compound COC1=CC=C2NC(C)=C(CC(O)=O)C2=C1 TXWGINUZLBAKDF-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
239000003435 antirheumatic agent Substances 0.000 claims description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000002524 organometallic group Chemical group 0.000 claims description 2
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
229960005141 piperazine Drugs 0.000 claims 4
IQYLNYFCJXRHTI-UHFFFAOYSA-N 5-benzamido-4-(dipropylamino)-5-oxopentanoic acid Chemical compound CCCN(CCC)C(CCC(O)=O)C(=O)NC(=O)C1=CC=CC=C1 IQYLNYFCJXRHTI-UHFFFAOYSA-N 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
230000009435 amidation Effects 0.000 claims 1
238000007112 amidation reaction Methods 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 22
239000000126 substance Substances 0.000 description 20
229960000905 indomethacin Drugs 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
230000000694 effects Effects 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 10
238000011156 evaluation Methods 0.000 description 10
239000000243 solution Substances 0.000 description 9
210000001519 tissue Anatomy 0.000 description 9
230000006378 damage Effects 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
230000000202 analgesic effect Effects 0.000 description 7
-1 chloro-propyl Chemical group 0.000 description 7
239000008188 pellet Substances 0.000 description 7
230000001154 acute effect Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
229920002683 Glycosaminoglycan Polymers 0.000 description 5
241000700159 Rattus Species 0.000 description 5
210000000988 bone and bone Anatomy 0.000 description 5
239000011575 calcium Substances 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
238000004364 calculation method Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
QBQNMIPDPJEZHR-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methoxymethyl]-2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1COCC1=CC=C(O)C(CC=2C=CC(O)=CC=2)=C1 QBQNMIPDPJEZHR-UHFFFAOYSA-N 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229940121363 anti-inflammatory agent Drugs 0.000 description 4
239000002260 anti-inflammatory agent Substances 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
230000000622 irritating effect Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000025865 Ulcer Diseases 0.000 description 3
229940124599 anti-inflammatory drug Drugs 0.000 description 3
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 3
239000006071 cream Substances 0.000 description 3
210000001156 gastric mucosa Anatomy 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000004452 microanalysis Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000003349 osteoarthritic effect Effects 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
229960002895 phenylbutazone Drugs 0.000 description 3
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
201000004384 Alopecia Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
241000252095 Congridae Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
206010015995 Eyelid ptosis Diseases 0.000 description 2
206010018691 Granuloma Diseases 0.000 description 2
102000057297 Pepsin A Human genes 0.000 description 2
108090000284 Pepsin A Proteins 0.000 description 2
108010047320 Pepsinogen A Proteins 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000000679 carrageenan Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229940113118 carrageenan Drugs 0.000 description 2
210000000845 cartilage Anatomy 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000029142 excretion Effects 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
150000002337 glycosamines Chemical class 0.000 description 2
208000024963 hair loss Diseases 0.000 description 2
230000003676 hair loss Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005259 measurement Methods 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
229940111202 pepsin Drugs 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
201000003004 ptosis Diseases 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000829 suppository Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
230000001562 ulcerogenic effect Effects 0.000 description 2
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
206010000087 Abdominal pain upper Diseases 0.000 description 1
208000012895 Gastric disease Diseases 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
210000001188 articular cartilage Anatomy 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000002805 bone matrix Anatomy 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
238000009795 derivation Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000008533 pain sensitivity Effects 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001373 regressive effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000000450 urinary calcium excretion Effects 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
230000001755 vocal effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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]

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CH1009075A 1974-08-12 1975-08-01 CH618697A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT69523/74A IT1043937B (it)	1974-08-12	1974-08-12	Defivati della n benzoil n' n' di ,n, propil, dl, isoglutamina ad attivita antiartrosioa ed antiin fiammatoria

Publications (1)

Publication Number	Publication Date
CH618697A5 true CH618697A5 (fr)	1980-08-15

Family

ID=11312323

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1009075A CH618697A5 (fr)	1974-08-12	1975-08-01

Country Status (15)

Country	Link
US (1)	US3985878A (fr)
JP (2)	JPS5416512B2 (fr)
AT (1)	AT345295B (fr)
BE (1)	BE830880A (fr)
CA (1)	CA1053663A (fr)
CH (1)	CH618697A5 (fr)
DE (1)	DE2535799C3 (fr)
ES (1)	ES440166A1 (fr)
FR (1)	FR2281755A1 (fr)
GB (1)	GB1467568A (fr)
HK (1)	HK38879A (fr)
IE (1)	IE42125B1 (fr)
IT (1)	IT1043937B (fr)
NL (1)	NL180663C (fr)
ZA (1)	ZA755107B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2338704A1 (fr) *	1976-01-21	1977-08-19	Roussel Uclaf	Nouveaux indoles substitues, leur procede de preparation et leur application comme medicament
DE2926472A1 (de) *	1979-06-30	1981-01-15	Thomae Gmbh Dr K	Neue benzoylderivate, deren herstellung und deren verwendung als arzneimittel
JPS61152656A (ja) *	1984-12-27	1986-07-11	Taiho Yakuhin Kogyo Kk	ピペラジン誘導体
KR900701752A (ko) *	1988-07-05	1990-12-06	이베 사치아끼	인돌 아세트산 유도체, 그의 제조법 및 이를 유효성분으로 하는 의약

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3669960A (en) *	1968-09-10	1972-06-13	Sumitomo Chemical Co	Novel amides of 3-indolylacetic acid

1974
- 1974-08-12 IT IT69523/74A patent/IT1043937B/it active Protection Beyond IP Right Term
- 1974-10-16 FR FR7434841A patent/FR2281755A1/fr active Granted
1975
- 1975-07-01 BE BE157883A patent/BE830880A/fr not_active IP Right Cessation
- 1975-07-10 US US05/594,914 patent/US3985878A/en not_active Expired - Lifetime
- 1975-07-11 CA CA231,281A patent/CA1053663A/fr not_active Expired
- 1975-07-30 NL NLAANVRAGE7509091,A patent/NL180663C/xx not_active IP Right Cessation
- 1975-08-01 CH CH1009075A patent/CH618697A5/it not_active IP Right Cessation
- 1975-08-04 ZA ZA00755107A patent/ZA755107B/xx unknown
- 1975-08-05 GB GB3274175A patent/GB1467568A/en not_active Expired
- 1975-08-07 IE IE1758/75A patent/IE42125B1/en unknown
- 1975-08-11 JP JP9743575A patent/JPS5416512B2/ja not_active Expired
- 1975-08-11 DE DE2535799A patent/DE2535799C3/de not_active Expired
- 1975-08-11 ES ES440166A patent/ES440166A1/es not_active Expired
- 1975-08-11 JP JP9743475A patent/JPS5416511B2/ja not_active Expired
- 1975-08-11 AT AT623775A patent/AT345295B/de not_active IP Right Cessation
1979
- 1979-06-14 HK HK388/79A patent/HK38879A/xx unknown

Also Published As

Publication number	Publication date
DE2535799A1 (de)	1976-02-26
ATA623775A (de)	1978-01-15
JPS5143773A (fr)	1976-04-14
BE830880A (fr)	1975-11-03
ZA755107B (en)	1976-07-28
AU8371775A (en)	1977-02-10
CA1053663A (fr)	1979-05-01
NL180663C (nl)	1987-04-01
ES440166A1 (es)	1977-05-16
FR2281755B1 (fr)	1978-07-28
DE2535799B2 (de)	1979-01-18
JPS5416512B2 (fr)	1979-06-22
GB1467568A (en)	1977-03-16
AT345295B (de)	1978-09-11
HK38879A (en)	1979-06-22
JPS5143774A (fr)	1976-04-14
IE42125L (en)	1976-02-12
IT1043937B (it)	1980-02-29
FR2281755A1 (fr)	1976-03-12
US3985878A (en)	1976-10-12
DE2535799C3 (de)	1979-09-13
NL7509091A (nl)	1976-02-16
IE42125B1 (en)	1980-06-04
JPS5416511B2 (fr)	1979-06-22

Legal Events

Date	Code	Title	Description
1993-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US20030114514A1 (en)	2003-06-19	Pharmaceutical compositions containing anti-beta 1 integrin compounds and uses
IT8149031A1 (it)	1983-02-03	Amidi organiche derivate da lipidi azotati utilizzabili come farmaci
DK151341B (da)	1987-11-23	Analogifremgangsmaade til fremstilling af d-phenylalanyl-l-prolyl-l-argininaldehydsulfat
JP5883863B2 (ja)	2016-03-15	プロテアーゼ活性化受容体の調節剤
CH658650A5 (it)	1986-11-28	Ammidi pirrolacetiche aventi attivita antiinfiammatoria.
FI85469C (fi)	1992-04-27	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-(4-hydroxi-3,5-di-tert -butylbenzoyl) homopiperazinderivat.
US20150057316A1 (en)	2015-02-26	Novel sulfonate-based trimebutine salts
CH618697A5 (fr)	1980-08-15
DE69416683T2 (de)	1999-08-12	Benzolactam-derivate
KR860001902B1 (ko)	1986-10-24	메르캅토 아실 카르니틴 에스테르류의 제조방법
FI67213C (fi)	1985-02-11	Foerfarande foer framstaellning av terapeutiskt anvaendbar n-(1'-allyl-2'-pyrrolidylmetyl)-2,3-dimetoxi-5-sulfamoylbensamid
Self et al.	1991	Romazarit. A potential disease-modifying antirheumatic drug
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
US4405607A (en)	1983-09-20	Novel pentapeptides, processes for their production, pharmaceutical compositions comprising said pentapeptides and their use
JPH06329538A (ja)	1994-11-29	皮膚疾患処置用薬剤
Awaad et al.	2017	Anti-ulcerogenic and anti-ulcerative colitis (UC) activities of seven amines derivatives
US20170216259A1 (en)	2017-08-03	Compositions and methods for targeting receptors expressed in the gut
US4166128A (en)	1979-08-28	Substituted phenylglycolic acid and its pharmaceutically acceptable esters and salts, and processes for preparing the same
IT9021443A1 (it)	1992-03-12	Derivati dell'acido 5-aminosalicilico (5-asa) per la terapia delle infiammazioni croniche intestinali
PL125527B1 (en)	1983-05-31	Process for preparing n-/1-methyl-2-pyrrolidylmethyl/-2,3-dimethoxy-5-methylsulfamylbenzamide
EP2600864B1 (fr)	2019-01-09	Compositions et procédés pour le traitement de maladies inflammatoires
US4923888A (en)	1990-05-08	Butenoic acid amides, their salts, and pharmaceutical compositions containing them
DE69312849T2 (de)	1998-01-08	Mercapto-acetamid-derivate
CZ695188A3 (en)	1993-07-14	ENOL ETHER OF 1,1-DIOXIDE OF 6-CHLORO-4-HYDROXY-2-METHYL-N- (2-PYRIDYL-2H-THIENO(2,3-c)-1,2-THIAZINECARBOXYLIC ACID AMIDE, PROCESS OF ITS PREPARATION AND ITS USE
US3761509A (en)	1973-09-25	N,n{40 -alkylenebis (4-substituted-benzamides)