Abstract: The present invention relates to novel chemical compounds, in particular cholest-4-en-3-one oxime derivatives and to the use thereof as medicaments, especially as cytoprotective medicaments, in particular neuroprotective, cardioprotective and/or hepatoprotective medicaments.

Abstract: The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-diene-11-methyleneoxyalkylenearyl derivative of the formula I with progesterone-antagonising action and to processes for preparation thereof, to use thereof for treatment and/or prophylaxis of disorders and to the use thereof for production of medicaments for treatment and/or prophylaxis of disorders, especially of fibroids of the uterus (myomas, uterine leiomyomas), endometriosis, heavy menstrual bleeds, meningiomas, hormone-dependent breast cancers and complaints associated with the menopause, or for fertility control and emergency contraception.

Abstract: A plurality of hip, ridge or rake shingles, and the shingles produced thereby and stacks and packages of such shingles are provided. An adhesive impregnated mat is moved longitudinally, and granules are provided onto adhesive, in predetermined bands. An overlay band of adhesive, continuous or discontinuous is provided, with granules thereon, increasing the thickness of the shingle material being made, in predetermined bands, relative to the remainder of the shingle material. The shingle material is slit longitudinally, and one portion can be laminated to another portion, preferably creating a multiple-ply laminated shingle material with thickened overlay portions and optionally with shadow line portions. The material is then slit longitudinally, and cut transversely into a plurality of hip, ridge or rake shingles, which may be individually separated from each other, or which may comprise a plurality of connected together shingles. The shingles are then stacked and wrapped.

Abstract: Disclosed are compounds having the general formula: wherein R1-R4 and X are as defined herein, pharmaceutical compositions including such compounds, and a method of treating a patient involving antagonizing the endogenous progesterone, such as in inducing menses and treating endometriosis, dysmenorrhea, endocrine hormone-dependent tumors, meningiomas, uterine leiomyomas, or uterine fibroids, inhibiting uterine endometrial proliferation, inducing cervical ripening, inducing labor, and in contraception.

Abstract: New aminooxime derivatives at position 3 of 2- and/or 4-substituted androstanes and androstenes, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of cardiovascular disorders, such as heart failure and hypertension. In particular compounds having the general formula (I) are described, where the radicals have the meanings described in detail in the application.

Abstract: This disclosure relates to progesterone derivatives and uses related thereto. In certain embodiments, the disclosure relates to compounds disclosed herein and uses for managing inflammation resulting from traumatic brain injury or stroke.

Abstract: The object of the invention is the use as a drug of a compound fitting formula I wherein X represents an oxygen atom or a ?N—OH group and R represents a group selected from or one of its esters and/or of its addition salts with pharmaceutically acceptable acids, particularly as a cytoprotective drug, preferentially a cardioprotective and/or neuroprotective drug, the compounds of formula I wherein R is R2, R3, R4, R5 or R6 as novel compounds as well as their preparation method and use.

Abstract: A method for providing neuroprotection to a patient in need of neuroprotection, comprising administering a neuroprotective-effective amount of a compound of formula I in which X is an oxygen atom or an ?N—OH group, R is selected from the group consisting of A is a hydrogen atom or together with B a carbon-carbon bond, B is a hydrogen atom, a hydroxy group or together with A a carbon-carbon bond, C is a hydrogen atom or together with D a carbon-carbon bond, D is a hydrogen atom or together with C a carbon-carbon bond, E is a hydrogen atom or together with F a carbon-carbon bond, F is a hydrogen atom or together with E a carbon-carbon bond, or an addition salt with a pharmaceutically acceptable acid.

Abstract: The invention features compounds, pharmaceutical compositions and methods useful for the treatment of neoplasia. In particular embodiments, the compounds of the invention are useful for the treatment of multidrug resistant neoplasia.

Abstract: The present disclosure provides methods and composition involving increased sensitivity of compounds using mass spectrometry. In one embodiment, a method of increasing the sensitivity for detection of a carbonyl group-containing compound by mass spectrometry can comprise derivatizing the carbonyl group-containing compound with an O-substituted hydroxylamine thereby producing an oxime, resulting in enhanced sensitivity of detection by mass spectrometry, as compared to the underivatized carbonyl group-containing compound. Additionally, a method for assaying a carbonyl group-containing compound can comprise reacting the carbonyl group-containing compound in a sample with an O-substituted hydroxylamine to produce an oxime and performing analysis with mass spectrometric detection of the oxime by a mass spectrometry instrument.

Abstract: The object of the invention is the use as a drug of a compound fitting formula I wherein X represents an oxygen atom or a ?N—OH group and R represents a group selected from or one of its esters and/or of its addition salts with pharmaceutically acceptable acids, particularly as a cytoprotective drug, preferentially a cardioprotective and/or neuroprotective drug, the compounds of formula I wherein R is R2, R3, R4, R5 or R6 as novel compounds as well as their preparation method and use.

Abstract: The present invention relates to novel chemical compounds, in particular cholest-4-en-3-one oxime derivatives and to the use thereof as medicaments, especially as cytoprotective medicaments, in particular neuroprotective, cardioprotective and/or hepatoprotective medicaments.

Abstract: Compound of formula I where X=O or ?N—OH group, R represents a group chosen from A=hydrogen or together with B a carbon-carbon bond, B=hydrogen, hydroxy or together with A a carbon-carbon bond, C, D, E, F=hydrogen or together with D a carbon-carbon bond, or the one of its addition salts with pharmaceutically acceptable acids, with the exception of a few compounds, as a medicament, use in particular as neuroprotectors, novel compounds of formula I and pharmaceutical compositions.

Abstract: New aminooxime derivatives at position 3 of 2- and/or 4-substituted androstanes and androstenes, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of cardiovascular disorders, such as heart failure and hypertension. In particular compounds having the general formula (I) are described, where the radicals have the meanings described in detail in the application.

Abstract: The invention relates to a process for the synthesis of d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime (also known as norelgestromin) via acetylation of d-norgestrel at position 17; oximation of the oxo group at position 3 of the obtained d-(17?)-13-ethyl-17-(acetyloxy)-18,19-dinorpregn-4-ene-20-yn-3-one; and then hydrolyzing the acetyloxy group at position 17 of the obtained d-(17?)-13-ethyl-17-(acetyloxy)-18,19-dinorpregn-4-ene-20-yn-3-oxime derivative, thereby obtaining norelgestromin.

Abstract: The invention is directed to a process of preparing substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3E- and -3Z-oxime isomers, as well as a process for the synthesis of the mixture of isomers and the pure isomers. The invention also relates to substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime and substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer. Further aspects of the invention include a composition comprising substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime or substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer, and methods of treatment using said compositions.

Abstract: New aminoalkoxyimino derivatives at position 3 of substituted B-homoandrostanes and B-heteroandrostanes, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of cardiovascular disorders, such as heart failure and hypertension. In particular compounds having the general formula (I) are described, where the radicals have the meanings described in detail in the application.

Abstract: The invention is directed to a process of preparing substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3E- and -3Z-oxime isomers, as well as a process for the synthesis of the mixture of isomers and the pure isomers. The invention also relates to substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime and substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer. Further aspects of the invention include a composition comprising substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime or substantially pure d-(17?)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer, and methods of treatment using said compositions.

Abstract: The object of the invention is the use as a drug of a compound fitting formula I wherein X represents an oxygen atom or a ?N—OH group and R represents a group selected from or one of its esters and/or of its addition salts with pharmaceutically acceptable acids, particularly as a cytoprotective drug, preferentially a cardioprotective and/or neuroprotective drug, the compounds of formula I wherein R is R2, R3, R4, R5 or R6 as novel compounds as well as their preparation method and use.

Abstract: Process for the preparation of Norelgestromin or 17?-hydroxy-13?-ethyl-18,19-dinorpregn-4-ene-20-yn-3-one oxime, also in crystalline form, in particular with an E/Z isomer ratio of between 1.3 and 1.5.

Abstract: The present invention is related to an oxime of the 13?-ethyl-17?-hydroxi-18,19-dinorpregn-4-en-20-in-3-o (norelgestromin) of Formula I with a relation of isomers E/Z between 1.3 and 1.6 and the method of producing the oxime.

Abstract: The present invention is related to an oxime of the 13&bgr;-ethyl-17&agr;-hydroxi-18,19-dinorpregn-4-en-20-in-3-o (norelgestromin) of Formula I with a relation of isomers E/Z between 1.3 and 1.

Abstract: Compounds of the general formula I 1

Abstract: The invention relates to (androst-5-en-17beta-yl)alkylsulfoxides and sulfones having general formula (I), wherein R1, R2, R3, X and Y are defined in the specification. The compounds of the invention have meiosis inhibiting activity and can be used for the control of fertility.

Abstract: The invention relates to 22R-hydroxycholesta-8,14-diene derivatives having general formula (I) wherein R1 is OR, OS03H or ═NOR; with R being H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alkyl; R4 is hydrogen, (C1-6)alkyl or (C1-6)acyl; R5 is hydrogen; or R5 designates, together with R6, an additional bond between the carbon atoms at which R5 and R6 are placed; R6 is hydrogen, hydroxy or halogen; or R6 designates, together with R5, an additional bond between the carbon atoms at which R6 and R5 are placed; each of R7 and R8 is independently hydrogen or (C1-4)alkyl, optionally substituted with OH, (C1-4)alkoxy, or halogen; or a pharmaceutically acceptable salt thereof. The compounds of the invention have meiosis inhibiting activity and can be used for the control of fertility.

Abstract: A process for the preparation of the compounds of general formula (I) in which R1 is H or OH; R2 is H, &agr;-OH, or &bgr;-OH; and R3 is a straight or branched C1-C4 alkyl group or a benzyl group, comprising the reduction of compounds of formula (III) wherein R1, R2 and R3 have the same meanings as in formula I, in the presence of sodium borohydride.

Abstract: An improved process is described for the preparation of compounds with general formula (I) and particularly for the preparation of the compound (E,Z) 3-(2-aminoethoxyimino)-androstane-6,17-dione, in which n=1 and R1=R2=H

Abstract: An androgenic steroid compound of the formula: wherein: X Y, Z, R1, R2, R3, R5 and R6 are as defined herein.

Abstract: A compound having the general formula: 1

Abstract: An androgenic steroid compound of the formula: 1

Abstract: An improved process is described for the preparation of compounds with general formula (I) and particularly for the preparation of the compound (E,Z) 3-(2-aminoethoxyimino)-androstane-6,17-dione, in which n=1 and R1=R2=H.

Abstract: The invention is directed to a novel class of steroids which exhibit potent antiprogestational activity.

Abstract: The invention relates to 17&bgr;-allyloxy(thio)alkyl-androstane derivatives having general formula (I) wherein R1 is (H, OR), (H, OSO3H) or NOR; with R being H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alkyl; n is 0, 1 or 2; X is O, S, S(O) or S(O)2; each of R4 and R5 is independently hydrogen or (C1-4)alkyl; each of R6, R7 and R8 is independently hydrogen, phenyl, halogen or (C1-4)alkyl, optionally substituted by hydroxy, (C1-4) alkoxy or halogen; or R7 and R8 together with the carbon atom to which they are bound form a (C3-6)cycloalkane ring; or R6 and R7 together with the carbon atoms to which they are bound form a (C5-6) cycloalkene ring; and wherein the dotted lines indicate a &Dgr;7 or a &Dgr;8 double bond, or a pair of conjugated double bonds selected from &Dgr;7,14, &Dgr;8,14 and &Dgr;6,8(14); or a pharmaceutically acceptable salt thereof. The compounds of the invention have meiosis activating activity and can be used for the control of fertility.

Abstract: The invention relates to compounds of the formula: in which R1, R2, R3, R4, R5, R6, n and X are as defined in the specification, and to pharmaceutical compositions containing them. These compounds are excellent progestogens which are devoid of residual androgenic activity.

Abstract: The invention relates to 20-aralkyl-5&agr;-pregnane derivative having general formula (I), or a pharmaceutically acceptable salt thereof, wherein R1 is (H,OR), (H,OSO3H) or NOR; R is H, (C1-6)alkyl or (C1-6)acyl; each of R2 and R3 is independently hydrogen or (C1-6)alkyl; X is a straight chain divalent C1-8 hydrocarbon radical, optionally comprising a double or a triple bond; or X is —(CH2)m—CR7R8—; m=0-4; at least one of R7 and R8 is (C1-4)alkyl, hydroxy, (C1-4)alkoxy or halogen; the other, if present, being hydrogen; or R7 and R8 together represent O or NOR′; R′ is H, (C1-6)alkyl or (C1-6)acyl; each of R4, R5 and R6 is independently hydrogen, hydroxy, (C1-4)alkoxy, halogen, NR9, R10 or (C1-4)alkyl, optionally substituted by hydroxy, alkoxy, halogen or oxo; each of R9 and R10 is independently hydrogen or (C1-4)alkyl; and the dotted lines indicate a &Dgr;7 or a &Dgr;8 double bond, or a pair of conjugated double bonds selected from &Dgr;7,14, &Dgr;8,14 and

Abstract: The invention is directed to a novel class of 17&bgr;-acyl-17&bgr;-propynyl steroids which exhibit potent antiprogestational activity.

Abstract: The invention is directed to 17.beta.-nitro-11.beta.-arylsteroids of formula I: ##STR1## wherein R.sup.1, R.sup.6, R.sup.7, R.sup.12 and X are as defined by the specification. The compounds exhibit potent antiprogestational activity and are useful in the treatment of fibroids, endometriosis, cervical ripening prior to delivery, hormone replacement therapy and in the control of fertility.

Abstract: Compounds of formula I ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings indicated in the description, are described, as well as processes for their production, pharmaceutical preparations containing these compounds as well as their use for treatment of diseases. The compounds have antigestagenic, antiglucocorticoid, antimineralocorticoid and antiandrogenic properties.

Abstract: The invention is drawn to a process for the preparation of a steroid of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and theo A, B, C, and D ring system has at least one double bond and is optionally substituted by at least one optionally protected hydroxy, optionally protected keto, halogen, alkyl and alkoxy of 1 to 4 carbon atoms, and alkenyl and alkynyl of 2 to 4 carbon atoms by reacting the corresponding 17-ketosteroid with a compound of the formula ##STR2## and then by reacting the resulting compound with an aryl sulfenyl halide. The intermediate produced then undergoes rearrangement followed by epimerization with a strong base to obtain a mixture of the corresponding sulfoxide diastereoisomers which is reacted with a thiophilic compound. The intermediate produced undergoes acid hydrolysis to provide the compound of formula I.

Abstract: The invention relates to a 11,21-bisphenyl-19-norpregnane derivative of formula I ##STR1## wherein R.sub.1 is selected from H, halogen, (1-6C)alkoxy, and NR.sub.5 R.sub.6, R.sub.5 and R.sub.6 being independently hydrogen or (1-6C)alkyl or R.sub.5 and R.sub.6 together are (3-6C)alkylene; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 together are a (1-3C)alkylenedioxy group, optionally substituted by one or more halogen atoms; R.sub.3 is methyl or ethyl; R.sub.4 is selected from C(O)-NR.sub.5 R.sub.6, SO.sub.n -(1-6C)alkyl optionally substituted by one or more halogen atoms, SO.sub.n -(3-6C)cycloalkyl, n being 1 or 2, SO.sub.2 -NR.sub.5 R.sub.6, 2-oxypyrrolidinyl, and NR.sub.5 R.sub.6 ; R.sub.7 is H or (1-6C)alkyl; R.sub.8 is H or carboxy-1-oxo(1-6C)alkyl; and X is selected from (H,OH), O, and NOH; 11 or a pharmaceutically acceptable salt thereof.The compounds of the invention have anti-glucocorticoid activity and can be used in treating or preventing glucocorticoid-dependent diseases.

Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.

Abstract: 17-hydroxyiminomethyl-14.beta.-hydroxy-5.beta.

Abstract: Novel compounds of the general formula I ##STR1## and the pharmacologically tolerable addition salts thereof with acids are described, in which eitherIa) R.sup.11 represents a hydrogen atom in the .beta.-configuration and each of R.sup.12 and R.sup.13 represents a hydrogen atom, orIb) R.sup.11 represents a hydrogen atom in the .beta.-configuration and R.sup.12 and R.sup.13 together represent a second bond, orIc) R.sup.11 and R.sup.12 together represent a second bond and R.sup.13 represents a hydrogen atom, orId) R.sup.11 represents a hydrogen atom in the .alpha.-configuration and R.sup.12 and R.sup.13 together represent a second bond,and in Ia), Ib), Ic) or Id)X represents an oxygen atom, the hydroxyimino grouping >N.about.OH or two hydrogen atoms,R.sup.1 represents a hydrogen atom or a methyl group,R.sup.2 represents a hydroxy group, a C.sub.1 -C.sub.10 -alkoxy group or a C.sub.1 -C.sub.10 -acyloxy group, andR.sup.3 and R.sup.

Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.

Abstract: New 11.beta.-phenyl-14.beta.H-steroids of general formula (I), where Z is an oxygen atom or the hydroxyimino-grouping N.about.OH, and M and N are either jointly a second compound or L is a hydrogen atom and M is an .alpha.-permanent hydroxy group and either A and B together are a second compound and D is a hydrogen atom, where R.sup.1 is a five or six-part heteroalkyl residue or a cycloalkyl, cycloalkenyl or aryl residue or A is a hydrogen atom and B and D together are a methylene bridge, where R.sup.1 besides the aforementioned residues may be a possibly substituted hydrocarbon residue with up to 10 C atoms, a possibly substituted amino group, a hydroxy or C.sub.1-8 alkoxy, mercapto or thioalkyl group, R.sup.2 is a methyl or ethyl residue, and R.sup.3 /R.sup.4 represents the usual combination of substituents on the C17 atom in steroid chemistry, having antigestagenic and other properties.

Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## and their non-toxic, pharmaceutically acceptable acid addition salts possessing a remarkable antiglucocorticoidal activity.

Abstract: 11.beta.-substituted-16.alpha., 17.alpha.-methylene-estra-4,9-dien-3-ones of formula I ##STR1## wherein R.sup.1 is a methyl or ethyl group;R.sup.2 is H; a C.sub.1-6 -alkyl, -alkoxymethyl, -alkanoyl or -alkoxcarbonyl group ; 2-methoxyethyl; 2-hydroxyethyl; 2-C.sub.1-4 -alkanoyloxyethyl; or a tri-C.sub.1-4 -alkylsilyl group;R.sup.3 is vinyl; a C.sub.1-6 -alkyl; or a phenyl radical para-substituted by --OCH.sub.3, --SCH.sub.3, --N(CH.sub.3), --CN, --CHO, CH.sub.3 CO--, CH.sub.3 CHOH-- or --CH.sub.2 OH;R.sup.6 is H or a C.sub.1-4 -alkyl group;X is O, a hydroxy- or methoxyimino group (.dbd.N.about.OH or --N.about.OCH.sub.3), or a cyclic thioketal with 2 or 3 carbon ring atomsare provided, as well as pharmaceutical compositions containing said compounds, methods of use of said compounds, and processes for their production.

Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl, alkylthio and haloalkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, optionally substituted arylthio of 6 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, acyl of an organic carboxylic acid of 1 to 12 carbon atoms, --CN, cycloalkyl of 3 to 6 carbon atoms and --(CH.sub.2).sub.m --Re, m is an integer from 1 to 3, Re is --OH or --SH or --Salk, Alk is alkyl of 1 to 6 carbon atoms, X is selected from the group consisting of oxygen, N--O--R.sub.1, ##STR2## or =X is H.sub.2 or ##STR3## R.sub.A and R.sub.B are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 6 carbon atoms, R.sub.1 is hydrogen or alkyl of 1 to 6 carbon, R' is hydrogen or acyl, the wavy lines indicate --or -position, Y is selected from the group consisting of oxygen, NOR, ##STR4## or =Y is ##STR5## H.sub.

Abstract: A 11.beta.-aryl-19-norprogesterone steroid of the formula: ##STR1## wherein (i) R.sup.1 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, OH, OC(O)CH.sub.3, or OC(O)R.sup.5 , wherein R.sup.5 is C.sub.2-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl or aryl, R.sub.2 is H, R.sup.3 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl, R.sup.4 is H, CH.sub.3, F or Cl, R.sup.6 is H, (CH.sub.3).sub.2 N, CH.sub.3 O, CH.sub.3 CO, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2, and X is O or NOCH.sub.3 ; or(ii) R.sup.1 and R.sup.2 taken together are a carbon-carbon bond and R.sup.3, R.sup.4, R.sup.6 and X are as defined above; or(iii) R.sup.1 and R.sup.3 taken together are --CH.sub.2 -- or --N.dbd.N--CH.sub.2 --, R.sup.2 is H and R.sup.4, R.sup.6 and X are as defined above; or(iv) R.sup.2 and R.sup.3 taken together are .dbd.CH.sub.2 and R.sup.1 , R.sup.4, R.sup.6 and X are as defined above.

Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.