E. R. Squibb Sons, Inc.

Jack Bernstein

Hans Hoehn

B Richard Vogt

Berthold Richard Vogt

Ravi K Varma

Frank L Weisenborn

Kathryn A Losee

Peter C Wade

Rudiger D Haugwitz

William A Slusarchyk

William H Koster

Barbara Stearns

Radiolabeled steroid derivatives having the formula ##STR1## wherein St is a des-hydroxy steroid moiety of (i) a hydroxy steroid intended for radioimmunoassay or (ii) a hydroxy containing derivative of a steroid intended for radio-immunoassay, said derivative having a strong affinity for the antibodies of the steroid intended for radioimmunoassay; R is hydrogen or alkyl of 1 to 3 carbon atoms; n is 0, 1, 2, 3 or 4 and the asterisk (*) indicates tagging with a radioisotope, are useful as tracers in radioimmunoassays.

Steroid derivatives and their use in radioimmunoassays

Radiolabeled steroid derivatives having the formula ##STR1## wherein St is a des-hydroxy steroid moiety of (i) a hydroxy steroid intended for radioimmunoassay or (ii) a hydroxy containing derivative of a steroid intended for radioimmunoassay, said derivative having a strong affinity for the antibodies of the steroid intended for radioimmunoassay; R is hydrogen or alkyl of 1 to 3 carbon atoms; n is 0, 1, 2, 3 or 4 and the asterisk (*) indicates tagging with a radioisotope, are useful as tracers in radioimmunoassays.

Radiolabeled steroid derivatives having the formula ##STR1## wherein St is des-hydroxy steroid moiety of (i) a hydroxy steroid intended for radioimmunoassay or (ii) a hydroxy containing derivative of a steroid intended for radioimmunoassay, said derivative having a strong affinity for the antibodies of the steroid intended for radioimmunoassay; R is hydrogen or alkyl of 1 to 3 carbon atoms; n is 0, 1, 2, 3 or 4 and the asterisk (*) indicates tagging with a radioisotope, are useful as tracers in radioimmunoassays.

Imidazolo-pyridine derivatives are provided having the structure ##STR1## wherein R is lower alkyl, lower alkenylalkyl, lower alkynylalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl or phenylalkyl and R.sup.1 is lower alkyl, phenylalkyl or di-lower alkylaminoalkyl and n is 0, 1 or 2. These compounds are useful as anthelmintic agents administered orally or parenterally.

Substituted imidazolo-pyridines and method

Radiolabeled vitamin B.sub.12 derivatives having the formula ##STR1## wherein R is hydrogen or alkyl of 1 to 3 carbon atoms; n is 0, 1, 2, 3 or 4; and the asterisk (*) indicates tagging with a radioisotope, are useful as tracers in radioassays.

Vitamin B.sub.12 derivative suitable for radiolabeling

The mercaptoacylpiperazine carboxylic acid compounds which have the formula ##STR1## wherein R, R.sub.3 and R.sub.4 each is hydrogen or lower alkyl;

Mercaptoacylpiperazine carboxylic acid compounds

Various 1,5,6,11-tetrahydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridine derivatives and their salts of the formulas ##STR1## wherein R.sub.1 is lower alkyl, phenyl, or phenyl-lower alkyl; R.sub.2 is hydrogen, lower alkyl or phenyl; R.sub.3 is hydrogen, halogen, or lower alkoxy; R.sub.4 is hydrogen, ##STR2## R.sub.5 is hydrogen or lower alkoxy; R.sub.6 is hydrogen, ##STR3## n is an integer from 2 to 6; R.sub.7 and R.sub.8 are the same or different and each is lower alkyl or R.sub.7 and R.sub.8 taken together with the N-atom form a heterocyclic ring of the formula ##STR4## wherein R.sub.9 is hydrogen or lower alkyl; R.sub.10 and R.sub.11 are the same or different and each is hydrogen or lower alkyl or R.sub.10 and R.sub.11 taken together with the N-atom form a heterocyclic ring of the formula ##STR5## wherein R.sub.9 is as defined above; are disclosed. These compounds possess useful anti-inflammatory activity as well as psychotropic activity.

1,5,6,11-Tetrahydro[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridine

New mercaptoacyl derivatives of heterocyclic carboxylic acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.

Mercaptoacylamino derivatives of heterocyclic carboxylic acids

New derivatives of 5,6-dihydrobenzo[5,6]cyclohepta-[1,2-b]pyrazolo[4,3-e]pyridin-11 (1H)-ones and imines, respectively, have the general formula ##STR1## They and the salts thereof are useful as psychotropic and antiinflammatory agents.

Derivatives of

Compounds of the formulas ##STR1## wherein R.sub.1 is lower alkyl, phenyl, benzyl or phenethyl; R.sub.2 is hydrogen, lower alkyl or phenyl; ##STR2## N IS AN INTEGER FROM 3 TO 6; R.sub.3 and R.sub.4 are each lower alkyl or R.sub.3 and R.sub.4 taken together with the N-atom form a heterocyclic ring of the formula ##STR3## wherein R.sub.5 is hydrogen, lower alkyl, or lower alkoxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. These compounds and their salts possess central nervous system activity and are useful as anti-anxiety agents.

Various

Various 1,5,6,11-tetrahydrobenzo[5,6]cyclohepta[1,2-b]-pyrazolo[4,3-e]pyridine derivatives and their salts of the formulas ##STR1## wherein R.sub.1 is lower alkyl, phenyl, or phenyl-lower alkyl; R.sub.2 is hydrogen, lower alkyl or phenyl; R.sub.3 is hydrogen, halogen, or lower alkoxy; R.sub.4 is hydrogen, ##STR2## ALKYL; R.sub.5 is hydrogen or lower alkoxy; R.sub.6 is hydrogen, ##STR3## n is an integer from 2 to 6; R.sub.7 and R.sub.8 are the same or different and each is lower alkyl or R.sub.7 and R.sub.8 taken together with the N-atom form a heterocyclic ring of the formula ##STR4## wherein R.sub.9 is hydrogen or lower alkyl; R.sub.10 and R.sub.11 are the same or different and each is hydrogen or lower alkyl or R.sub.10 and R.sub.11 taken together with the N-atom form a heterocyclic ring of the formula ##STR5## wherein R.sub.9 is as defined above; are disclosed. These compounds possess useful antiinflammatory activity as well as psychotropic activity.

1,5,6,11-Tetrahydro[5,6]cyclohepta-[1,2,-b]pyrazolo[4,3-e]pyridine

Compounds of the formulas ##STR1## wherein R.sub.1 is lower alkyl, phenyl, benzyl or phenethyl; R.sub.2 is hydrogen, lower alkyl or phenyl; R is ##STR2## N IS AN INTEGER FROM 3 TO 6; R.sub.3 and R.sub.4 are each lower alkyl or R.sub.3 and R.sub.4 taken together with the N-atom form a heterocyclic ring of the formula ##STR3## wherein R.sub.5 is hydrogen, lower alkyl, or lower alkoxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. These compounds and their salts possess central nervous system activity and are useful as anti-anxiety agents.

1,5,10,11-Tetrahydrobenzo[4,5]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridines

New derivatives of 5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-ones and imines, respectively, have the general formula ##STR1## They and the salts thereof are useful as psychotropic and antiinflammatory agents.

Compounds of the formulas wherein R.sub.1 is lower alkyl, phenyl, benzyl or phenethyl; R.sub.2 is hydrogen, lower alkyl or phenyl; R is ##STR1## N IS AN INTEGER FROM 3 TO 6; R.sub.3 and R.sub.4 are each lower alkyl or R.sub.3 and R.sub.4 taken together with the N-atom form a heterocyclic ring of the formula ##STR2## wherein R.sub.5 is hydrogen, lower alkyl, or lower alkoxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. These compounds and their salts possess central nervous system activity and are useful as anti-anxiety agents.

Various 1,5,10,11-tetrahydrobenzo [4,5]-cyclohepta

New derivatives of 10,11-dihydrobenzo[4,5]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)ones have the general formula ##STR1## They and salts thereof are useful as psychotropic agents.

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New Brunswick, NJ, United States of America

Jack Bernstein