DE1667925A1 - Arzneimittel - Google Patents

Arzneimittel

Info

Publication number: DE1667925A1
Authority: DE; Germany
Prior art keywords: pyridyl; amines; beta; alkyl; cyclobutane
Prior art date: 1967-03-09
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.): Pending

Application number

DE19681667925

Other languages

German (de)

English (en)

Inventor

Schayer Richard William

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.)

Unimed Inc

Original Assignee

Unimed Inc

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.)

1967-03-09

Filing date

1968-01-15

Publication date

1971-07-22

1968-01-15 Application filed by Unimed Inc filed Critical Unimed Inc

1971-07-22 Publication of DE1667925A1 publication Critical patent/DE1667925A1/de

Status Pending legal-status Critical Current

Links

239000003814 drug Substances 0.000 title claims description 11
229940079593 drug Drugs 0.000 title claims description 7
239000003246 corticosteroid Substances 0.000 claims description 39
230000000694 effects Effects 0.000 claims description 36
229960001334 corticosteroids Drugs 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 12
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
230000002378 acidificating effect Effects 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 7
230000003000 nontoxic effect Effects 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 16
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 8
-1 alkyl amides Chemical class 0.000 description 8
229960000890 hydrocortisone Drugs 0.000 description 8
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 7
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
229960004544 cortisone Drugs 0.000 description 7
229960001340 histamine Drugs 0.000 description 6
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
QLSJOGIENLKPTF-WLHGVMLRSA-N (e)-but-2-enedioic acid;pyridine Chemical compound C1=CC=NC=C1.OC(=O)\C=C\C(O)=O QLSJOGIENLKPTF-WLHGVMLRSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000000034 method Methods 0.000 description 4
239000002674 ointment Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
UUQMNUMQCIQDMZ-UHFFFAOYSA-N betahistine Chemical compound CNCCC1=CC=CC=N1 UUQMNUMQCIQDMZ-UHFFFAOYSA-N 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
229940088597 hormone Drugs 0.000 description 3
239000005556 hormone Substances 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
229960004618 prednisone Drugs 0.000 description 3
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
208000038016 acute inflammation Diseases 0.000 description 2
230000006022 acute inflammation Effects 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000006378 damage Effects 0.000 description 2
229960003957 dexamethasone Drugs 0.000 description 2
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
208000014674 injury Diseases 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
210000004400 mucous membrane Anatomy 0.000 description 2
XQSBKDIZHIJPQI-UHFFFAOYSA-N n,n-diethyl-2-pyridin-2-ylethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCC1=CC=CC=N1 XQSBKDIZHIJPQI-UHFFFAOYSA-N 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
210000000329 smooth muscle myocyte Anatomy 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
FUFLCEKSBBHCMO-KJQYFISQSA-N 11-dehydrocorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 FUFLCEKSBBHCMO-KJQYFISQSA-N 0.000 description 1
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
CGTWPKMZGWJCGE-UHFFFAOYSA-N 2-pyridin-2-ylethanamine;hydrochloride Chemical compound Cl.NCCC1=CC=CC=N1 CGTWPKMZGWJCGE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010000410 Acetonaemia Diseases 0.000 description 1
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
206010018473 Glycosuria Diseases 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010021067 Hypopituitarism Diseases 0.000 description 1
208000007976 Ketosis Diseases 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
206010028980 Neoplasm Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 description 1
208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 description 1
244000233952 Polygonum bistorta Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
206010041277 Sodium retention Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
229960002478 aldosterone Drugs 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
229940031955 anhydrous lanolin Drugs 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
229960001392 betahistine hydrochloride Drugs 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
229960000258 corticotropin Drugs 0.000 description 1
229940066351 cortisone 10 mg Drugs 0.000 description 1
229960003290 cortisone acetate Drugs 0.000 description 1
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
229960002344 dexamethasone sodium phosphate Drugs 0.000 description 1
PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
230000000642 iatrogenic effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
GGNCWMWEFFOIPH-UHFFFAOYSA-N methanamine;propane Chemical compound NC.CCC GGNCWMWEFFOIPH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
PIIWYFURBFSHKM-UHFFFAOYSA-N n-methyl-2-pyridin-2-ylethanamine;hydrochloride Chemical compound Cl.CNCCC1=CC=CC=N1 PIIWYFURBFSHKM-UHFFFAOYSA-N 0.000 description 1
QZBUGNURVLWJPK-UHFFFAOYSA-N n-methyl-2-pyridin-4-ylethanamine Chemical compound CNCCC1=CC=NC=C1 QZBUGNURVLWJPK-UHFFFAOYSA-N 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
208000015380 nutritional deficiency disease Diseases 0.000 description 1
235000019271 petrolatum Nutrition 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
239000002504 physiological saline solution Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229940102542 prednisone 5 mg Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
208000004124 rheumatic heart disease Diseases 0.000 description 1
201000000306 sarcoidosis Diseases 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940074404 sodium succinate Drugs 0.000 description 1
210000005070 sphincter Anatomy 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001457 vasomotor Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (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)
Steroid Compounds (AREA)

DE19681667925 1967-03-09 1968-01-15 Arzneimittel Pending DE1667925A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US62179167A	1967-03-09	1967-03-09

Publications (1)

Publication Number	Publication Date
DE1667925A1 true DE1667925A1 (de)	1971-07-22

Family

ID=24491653

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19681667925 Pending DE1667925A1 (de)	1967-03-09	1968-01-15	Arzneimittel

Country Status (9)

Country	Link
US (1)	US3474168A (xx)
BE (1)	BE710504A (xx)
DE (1)	DE1667925A1 (xx)
FR (1)	FR7356M (xx)
GB (1)	GB1175482A (xx)
IE (1)	IE31885B1 (xx)
IL (1)	IL29319A (xx)
NL (1)	NL6801136A (xx)
SE (1)	SE347874B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4353896A (en) *	1981-06-08	1982-10-12	Levy Michael A	Penetrating topical medicament
US5358943A (en) *	1987-12-29	1994-10-25	Clark Abbot F	Use of tetrahydrocortisol to prevent elevations in intraocular pressure caused by corticosteroids
US4945089A (en) *	1987-12-29	1990-07-31	Alcon Laboratories, Inc.	Use of tetrahydrocortexolone to prevent elevations in intraocular pressure caused by corticosteroids
US20060074063A1 (en) *	1995-12-29	2006-04-06	Fernandez-Pol Jose A	Pharmacological agent and method of treatment

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2794763A (en) *	1955-01-27	1957-06-04	Pfizer & Co C	Pressor amines
US3105010A (en) *	1959-06-19	1963-09-24	Schering Corp	Steroid-amino acid compositions for preventing negative nitrogen balance
US3415833A (en) *	1964-04-16	1968-12-10	Unimed Inc	Pyridyl-dicarboxylic acid cyclobutane derivatives
US3984304A (en) *	1974-11-11	1976-10-05	Ppg Industries, Inc.	Electrode unit

1967
- 1967-03-09 US US621791A patent/US3474168A/en not_active Expired - Lifetime
1968
- 1968-01-15 GB GB2078/68A patent/GB1175482A/en not_active Expired
- 1968-01-15 DE DE19681667925 patent/DE1667925A1/de active Pending
- 1968-01-17 IL IL29319A patent/IL29319A/en unknown
- 1968-01-19 SE SE00763/68A patent/SE347874B/xx unknown
- 1968-01-23 IE IE93/68A patent/IE31885B1/xx unknown
- 1968-01-25 NL NL6801136A patent/NL6801136A/xx unknown
- 1968-02-08 BE BE710504D patent/BE710504A/xx unknown
- 1968-02-20 FR FR140522A patent/FR7356M/fr not_active Expired

Also Published As

Publication number	Publication date
BE710504A (xx)	1968-06-17
SE347874B (xx)	1972-08-21
GB1175482A (en)	1969-12-23
IE31885B1 (en)	1973-02-07
US3474168A (en)	1969-10-21
NL6801136A (xx)	1968-09-10
FR7356M (xx)	1969-10-20
IL29319A (en)	1971-11-29
IE31885L (en)	1968-09-09

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